Login Register Cart 0
Generic placeholder image

Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

Chemistry of Unsymmetrical C1-Substituted Oxabenzonorbornadienes

Author(s): Austin Pounder, Angel Ho, Matthew Macleod and William Tam*

Volume 18, Issue 5, 2021

Published on: 05 January, 2021

Page: [446 - 474] Pages: 29

DOI: 10.2174/1570179417666210105121115

Price: $65

Abstract

Oxabenzonorbornadiene (OBD) is a useful synthetic intermediate, which can be readily activated by transition metal complexes with great face selectivity due to its dual-faced nature and intrinsic angle strain on the alkene. To date, the understanding of transition-metal catalyzed reactions of OBD itself has burgeoned; however, this has not been the case for unsymmetrical OBDs. Throughout the development of these reactions, the nature of C1-substituent has proven to have a profound effect on both the reactivity and selectivity of the outcome of the reaction. Upon substitution, different modes of reactivity arise, contributing to the possibility of multiple stereo-, regio-, and in extreme cases, constitutional isomers, which can provide unique means of constructing a variety of synthetically useful cyclic frameworks. To maximize selectivity, an understanding of bridgehead substituent effects is crucial. To that end, this review outlines hitherto reported examples of bridgehead substituent effects on the chemistry of unsymmetrical C1-substituted OBDs.

Keywords: Oxabenzonorbornadiene, unsymmetrical oxabenzonorbornadiene, transition-metal-catalysis, ring-opening, cycloaddition, isomerization, substituent effects, regioselectivity.

« Previous Next »
Graphical Abstract

[1]
Caple, R.; Chen, G.; Nelson, J. Electrophilic approach on norborene systems. preferential endo attack of halogens on hindered 2-phenylnorbornenes. J. Org. Chem., 1971, 36(19), 2870.
[http://dx.doi.org/10.1021/jo00818a031]
[2]
Howell, J.; Goddard, J.D.; Tam, W. a relative approach for determining ring strain energies of heterobicyclic alkene. Tetrahedron, 2009, 65(23), 4562.
[http://dx.doi.org/10.1016/j.tet.2009.03.090]
[3]
García-García, P.; Fernández-Rodríguez, M.A.; Rocaboy, C.; Andina, F.; Aguilar, E. a sub-stoichiometric tungsten-mediated pauson-khand reaction: Scope and limitations. J. Organomet. Chem., 2008, 693(18), 3092.
[http://dx.doi.org/10.1016/j.jorganchem.2008.06.032]
[4]
Fan, B.M.; Li, X.J.; Peng, F.Z.; Zhang, H.B.; Chan, A.S.; Shao, Z.H. Ligand-controlled enantioselective [2 + 2] cycloaddition of oxabicyclic alkenes with terminal alkynes using chiral iridium catalysts. Org. Lett., 2010, 12(2), 304-306.
[http://dx.doi.org/10.1021/ol902574c] [PMID: 20025256]
[5]
Park, S.H.; Wang, S.G.; Cramer, N. Enantioselective Ruthenium(II)-catalyzed access to benzonorcaradienes by coupling of oxabenzonorbornadienes and alkynes. ACS Catal., 2019, 9(11), 10226.
[http://dx.doi.org/10.1021/acscatal.9b03858]
[6]
Dey, A.; Rathi, A.; Volla, C.M.R. cobalt(iii)-catalyzed [4+2] annulation of heterobicyclic alkenes by Sp2 C−H activation. Asian J. Org. Chem., 2018, 7(7), 1362.
[http://dx.doi.org/10.1002/ajoc.201800251]
[7]
Mo, D.L.; Yuan, T.; Ding, C.H.; Dai, L.X.; Hou, X.L. Palladacycle-catalyzed methylenecyclopropanation of bicyclic alkenes with propiolates. J. Org. Chem., 2013, 78(22), 11470-11476.
[http://dx.doi.org/10.1021/jo402024v] [PMID: 24128061]
[8]
Pei, B.J.; Lee, A.W.M. Highly efficient synthesis of extended triptycenes via diels-alder cycloaddition in water under microwave radiation. Tetrahedron Lett., 2010, 51(34), 4519.
[http://dx.doi.org/10.1016/j.tetlet.2010.06.097]
[9]
Ge, G.C.; Mo, D.L.; Ding, C.H.; Dai, L.X.; Hou, X.L. Palladacycle-catalyzed reaction of bicyclic alkenes with terminal ynones: regiospecific synthesis of polysubstituted furans. Org. Lett., 2012, 14(22), 5756-5759.
[http://dx.doi.org/10.1021/ol302586m] [PMID: 23145937]
[10]
Cheng, Y.; Parthasarathy, K.; Bolm, C. Rhodium(III)-Catalyzed annulation of n-methoxybenzamides with heterobicyclic alkenes by c–h functionalization: Synthesis of Benzo. [b] Phenanthridinones. Eur. J. Org. Chem., 2017, 2017(8), 1203.
[http://dx.doi.org/10.1002/ejoc.201700029]
[11]
Wender, P.A.; Croatt, M.P.; Kühn, B. Rhodium(I)-Catalyzed [2+2], [2+2+2], and [2+2+2+2] Cycloadditions of Dienes or Alkynes with a Bis-Ene. Organometallics, 2009, 28(20), 5841.
[http://dx.doi.org/10.1021/om9007373]
[12]
Margetić, D.; Trošelj, P.; Murata, Y. Microwave-accelerated ruthenium-catalyzed [2π+2π] cycloadditions of dimethylacetylene dicarboxylate with norbornenes. Synth. Commun., 2011, 41(8), 1239.
[http://dx.doi.org/10.1080/00397911.2010.481744]
[13]
Gandeepan, P.; Rajamalli, P.; Cheng, C.H. Diastereoselective [3+2] annulation of aromatic/vinylic amides with bicyclic alkenes through cobalt-catalyzed C-H Activation and intramolecular nucleophilic addition. Angew. Chem. Int. Ed. Engl., 2016, 55(13), 4308-4311.
[http://dx.doi.org/10.1002/anie.201512018] [PMID: 26914532]
[14]
Zhang, S.W.; Kaneko, T.; Takahashi, S. Rhodium-Catalyzed copolymerization of norbornadienes and norbornenes with carbon monoxide. Macromolecules, 2000, 33(19), 6930.
[http://dx.doi.org/10.1021/ma000510d]
[15]
Fillion, E.; Trépanier, V.E.; Mercier, L.G.; Remorova, A.A.; Carson, R.J. Oxidative Coupling of 2-Substituted 1,2-Dihydro-1-Naphthols Using Jones Reagent: A Simple Entry into 3,3′-Disubstituted 1,1′-Binaphthyl-4, 4′-Diols. Tetrahedron Lett., 2005, 46(7), 1091.
[http://dx.doi.org/10.1016/j.tetlet.2004.12.099]
[16]
De Lucchi, O.; Daştan, A.; Altundaş, A.; Fabris, F.; Balci, M. Cyclotrimerization of “Oxabenzonorbornadiene”: Synthesis of Syn- and Anti-5,6,11,12,17,18-Hexahydro-5,18:6,11:12,17-Triepoxytrinaphthylene. Helv. Chim. Acta, 2004, 87(9), 2364.
[http://dx.doi.org/10.1002/hlca.200490213]
[17]
Huang, D.J.; Cheng, C.H. [2 + 2] dimerization of norbornadiene and its derivatives in the presence of nickel complexes and zinc metal. J. Organomet. Chem., 1995, 490(1), C1.
[http://dx.doi.org/10.1016/0022-328X(94)05335-9]
[18]
Sawama, Y.; Ogata, Y.; Kawamoto, K.; Satake, H.; Shibata, K.; Monguchi, Y.; Sajiki, H.; Kita, Y. Lewis acid-catalyzed ring-opening functionalizations of 1,4-epoxy-1,4-dihydronaphthalenes. Adv. Synth. Catal., 2013, 355(2), 517.
[http://dx.doi.org/10.1002/adsc.201200771]
[19]
Sun, Y.W.; Xu, Q.; Shi, M. Gold-catalyzed reaction of oxabicyclic alkenes with electron-deficient terminal alkynes to produce acrylate derivatives. Beilstein J. Org. Chem., 2013, 9, 1969-1976.
[http://dx.doi.org/10.3762/bjoc.9.233] [PMID: 24204408]
[20]
Shang, M.; Butler, D.N.; Warrener, R.N.; Margetić, D. Rack-Mounted Chemistry IV: The Thermal Rearrangement of 7-Oxabenzonorbornadienes into Benzo[b]Oxepines on and off the Polycyclic Rack. Tetrahedron Lett., 2013, 54(39), 5335.
[http://dx.doi.org/10.1016/j.tetlet.2013.07.105]
[21]
Lu, Z.; Zhang, H.; Yang, Z.; Ding, N.; Meng, L.; Wang, J. Asymmetric hydrophosphination of heterobicyclic alkenes: facile access to phosphine ligands for asymmetric catalysis. ACS Catal., 2019, 9(2), 1457.
[http://dx.doi.org/10.1021/acscatal.8b04787]
[22]
Dengiz, C.; Çalişkan, R.; Balci, M. Chloroacetonylation of C=C Double Bonds Promoted by Manganese(III). Acetate. Tetrahedron Lett., 2012, 53(5), 550.
[http://dx.doi.org/10.1016/j.tetlet.2011.11.098]
[23]
Yang, T.; Lu, L.; Shen, Q. Iron-mediated Markovnikov-selective hydro-trifluoromethylthiolation of unactivated alkenes. Chem. Commun. (Camb.), 2015, 51(25), 5479-5481.
[http://dx.doi.org/10.1039/C4CC08655D] [PMID: 25487645]
[24]
Cui, B.; Sun, H.; Xu, Y.; Li, L.; Duan, L.; Li, Y.M. Mn(OAc)3-Mediated hydrotrifluoromethylation of unactivated alkenes using cf3so2na as the trifluoromethyl source. J. Org. Chem., 2018, 83(11), 6015-6024.
[http://dx.doi.org/10.1021/acs.joc.8b00633] [PMID: 29733609]
[25]
Mannathan, S.; Cheng, C.H. Nickel-catalyzed regio- and diastereoselective intermolecular three-component coupling of oxabicyclic alkenes with alkynes and organoboronic acids. Chem. Commun. (Camb.), 2013, 49(15), 1557-1559.
[http://dx.doi.org/10.1039/c2cc38001c] [PMID: 23325053]
[26]
Hulcoop, D.G.; Lautens, M. Palladium-catalyzed annulation of aryl heterocycles with strained alkenes. Org. Lett., 2007, 9(9), 1761-1764.
[http://dx.doi.org/10.1021/ol070475w] [PMID: 17407300]
[27]
Lv, W.; Yu, J.; Ge, B.; Wen, S.; Cheng, G. Palladium-catalyzed catellani-type bis-silylation and bis-germanylation of aryl iodides and norbornenes. J. Org. Chem., 2018, 83(20), 12683-12693.
[http://dx.doi.org/10.1021/acs.joc.8b02018] [PMID: 30235929]
[28]
Prakash, S.; Chang, Y.C.; Cheng, C.H. Rhenium(I)-Catalyzed ortho-C-H Addition to Bicyclic Alkenes. Chem. Asian J., 2018, 13(13), 1664-1668.
[http://dx.doi.org/10.1002/asia.201800433] [PMID: 29676048]
[29]
Zhou, Y.; Yu, L.; Chen, J.; Xu, J.; He, Z.; Shen, G.; Fan, B. Rhodium-Catalyzed Asymmetric Cyclization/Addition Reactions of 1,6-Enynes and Oxa/Azabenzonorbornadienes. Org. Lett., 2018, 20(5), 1291-1294.
[http://dx.doi.org/10.1021/acs.orglett.7b04044] [PMID: 29436838]
[30]
Cheng, H.; Dong, W.; Dannenberg, C.A.; Dong, S.; Guo, Q.; Bolm, C. Ruthenium-Catalyzed Hydroarylations of Oxa- and Azabicyclic Alkenes. ACS Catal., 2015, 5(5), 2770.
[http://dx.doi.org/10.1021/acscatal.5b00258]
[31]
Wu, X.; Chu, L.; Qing, F.L. Silver-catalyzed hydrotrifluoromethylation of unactivated alkenes with CF3SiMe3. Angew. Chem. Int. Ed. Engl., 2013, 52(8), 2198-2202.
[http://dx.doi.org/10.1002/anie.201208971] [PMID: 23341119]
[32]
Mizumura, M.; Shinokubo, H.; Osuka, A. Synthesis of chiral porphyrins through Pd-catalyzed [3+2] annulation and heterochiral self-assembly. Angew. Chem. Int. Ed. Engl., 2008, 47(29), 5378-5381.
[http://dx.doi.org/10.1002/anie.200801269] [PMID: 18548473]
[33]
Sewano, T.; Ou, K.; Nishimura, T.; Hayashi, T. Cobalt-Catalyzed Asymmetric Addition of Silylacetylenes to Oxa- and Azabenzonorbornadienes. Chem. Commun. (Camb.), 2012, 48(48), 5956.
[http://dx.doi.org/10.1039/c2cc31880f] [PMID: 22576233]
[34]
Valiulin, R.A.; Mamidyala, S.; Finn, M.G. Taming chlorine azide: access to 1,2-azidochlorides from alkenes. J. Org. Chem., 2015, 80(5), 2740-2755.
[http://dx.doi.org/10.1021/acs.joc.5b00009] [PMID: 25719396]
[35]
Çalışkan, R.; Nohut, N.; Yılmaz, Ö.; Sahin, E.; Balci, M. Unusual manganese(III)-mediated oxidative free-radical additions of meldrum’s acid and dimethyl malonate to benzonorbornadiene and oxabenzonorbornadiene. Tetrahedron, 2017, 73(4), 291.
[http://dx.doi.org/10.1016/j.tet.2016.11.061]
[36]
Liu, M.; Niu, J.L.; Yang, D.; Song, M.P. Development of a Traceless Directing Group. Development of a Traceless Directing Group: Cp*-Free Cobalt-Catalyzed C-H Activation/Annulations to Access Isoquinolinones. J. Org. Chem., 2020, 85(6), 4067-4078.
[http://dx.doi.org/10.1021/acs.joc.9b03073] [PMID: 32049523]
[37]
Yang, S.Y.; Han, W.Y.; He, C.; Cui, B.D.; Wan, N.W.; Chen, Y.Z. 2,2-Bifunctionalization of Norbornene in Palladium-Catalyzed Domino Annulation. Org. Lett., 2019, 21(21), 8857-8860.
[http://dx.doi.org/10.1021/acs.orglett.9b03565] [PMID: 31638817]
[38]
Wang, P.; Xu, Y.; Sun, J.; Li, X. Rhodium(III)-Catalyzed Chemo-divergent Couplings of Sulfoxonium Ylides with Oxa/azabicyclic Olefins. Org. Lett., 2019, 21(20), 8459-8463.
[http://dx.doi.org/10.1021/acs.orglett.9b03226] [PMID: 31588755]
[39]
Lee, H.; Lee, B.Y.; Yun, J. Copper(I)-taniaphos catalyzed enantiodivergent hydroboration of bicyclic alkenes. Org. Lett., 2015, 17(3), 764-766.
[http://dx.doi.org/10.1021/ol503598w] [PMID: 25603172]
[40]
Gong, T.J.; Yu, S.H.; Li, K.; Su, W.; Lu, X.; Xiao, B.; Fu, Y. Copper-Catalyzed Alkynylboration of Alkenes with Diboron Reagents and Bromoalkynes. Chem. Asian J., 2017, 12(22), 2884-2888.
[http://dx.doi.org/10.1002/asia.201701176] [PMID: 28949438]
[41]
Huang, Y.; Smith, K.B.; Brown, M.K. Copper-Catalyzed Borylacylation of Activated Alkenes with Acid Chlorides. Angew. Chem. Int. Ed. Engl., 2017, 56(43), 13314-13318.
[http://dx.doi.org/10.1002/anie.201707323] [PMID: 28849603]
[42]
Miki, Y.; Hirano, K.; Satoh, T.; Miura, M. Copper-catalyzed enantioselective formal hydroamination of oxa- and azabicyclic alkenes with hydrosilanes and hydroxylamines. Org. Lett., 2014, 16(5), 1498-1501.
[http://dx.doi.org/10.1021/ol5003219] [PMID: 24555736]
[43]
Sadeer, A.; Ong, Y.J.; Kojima, T.; Foo, C.Q.; Li, Y.; Pullarkat, S.A.; Leung, P.H. Desymmetrization of Achiral Heterobicyclic Alkenes through Catalytic Asymmetric Hydrophosphination. Chem. Asian J., 2018, 13(19), 2829-2833.
[http://dx.doi.org/10.1002/asia.201801061] [PMID: 30022614]
[44]
Li, D.Y.; Huang, Z.L.; Liu, P.N. Heterobicyclic Core Retained Hydroarylations through C-H Activation: Synthesis of Epibatidine Analogues. Org. Lett., 2018, 20(7), 2028-2032.
[http://dx.doi.org/10.1021/acs.orglett.8b00571] [PMID: 29558151]
[45]
Hu, J.; Yang, Q.; Xu, J.; Huang, C.; Fan, B.; Wang, J.; Lin, C.; Bian, Z.; Chan, A.S.C. Iridium-catalyzed asymmetric hydroalkynylation reactions of oxabenzonorbornadienes. Org. Biomol. Chem., 2013, 11(5), 814-820.
[http://dx.doi.org/10.1039/C2OB26775F] [PMID: 23229014]
[46]
Chen, J.; Liu, S.; Zhou, Y.; Li, S.; Lin, C.; Bian, Z.; Fan, B. Palladium/Silver-Cocatalyzed Tandem Reactions of Oxabenzonorbornadienes with Substituted Arylacetylenes: A Simple Method for the Preparation of 1,2-Diarylethanones and 1,2-Diarylacetylenes. Organometallics, 2015, 34(17), 4318.
[http://dx.doi.org/10.1021/acs.organomet.5b00551]
[47]
Ma, F.; Chen, J.; Yang, F.; Shinde, M.V.; Zhou, Y.; Fan, B. Palladium/zinc co-catalyzed asymmetric transfer hydrogenation of oxabenzonorbornadienes with alcohols as hydrogen sources. Org. Biomol. Chem., 2017, 15(11), 2359-2362.
[http://dx.doi.org/10.1039/C7OB00175D] [PMID: 28256675]
[48]
Endo, K.; Tanaka, K.; Ogawa, M.; Shibata, T. Multinuclear Pd/Zn complex-catalyzed asymmetric alkylative ring-opening reaction of oxabicyclic alkenes. Org. Lett., 2011, 13(5), 868-871.
[http://dx.doi.org/10.1021/ol102928q] [PMID: 21261272]
[49]
Wu, M.S.; Rayabarapu, D.K.; Cheng, C.H. Nickel-catalyzed addition of alkenylzirconium reagents to bicyclic olefins: a highly regio- and stereoselective ring-opening reaction. J. Org. Chem., 2004, 69(24), 8407-8412.
[http://dx.doi.org/10.1021/jo048721u] [PMID: 15549814]
[50]
Rayabarapu, D.K.; Cheng, C-H. Novel Cyclization and Reductive Coupling of Bicyclic Olefins with Alkyl Propiolates Catalyzed by Nickel Complexes. Pure Appl. Chem., 2007, 74(1), 69.
[http://dx.doi.org/10.1351/pac200274010069]
[51]
Tsui, G.C.; Tsoung, J.; Dougan, P.; Lautens, M. One-pot synthesis of chiral dihydrobenzofuran framework via Rh/Pd catalysis. Org. Lett., 2012, 14(21), 5542-5545.
[http://dx.doi.org/10.1021/ol302646a] [PMID: 23061656]
[52]
Zhang, T.K.; Yuan, K.; Hou, X.L. Palladacycle as Highly Efficient Catalyst for Ring Opening of Oxabicyclic Alkenes with Organozinc Halides. J. Organomet. Chem., 2007, 692(10), 1912.
[http://dx.doi.org/10.1016/j.jorganchem.2006.12.039]
[53]
Rayabarapu, D.K.; Chiou, C.F.; Cheng, C.H. Highly stereoselective ring-opening addition of terminal acetylenes to bicyclic olefins catalyzed by nickel complexes. Org. Lett., 2002, 4(10), 1679-1682.
[http://dx.doi.org/10.1021/ol025731d] [PMID: 12000272]
[54]
Cabrera, S.; Gómez Arrayás, R.; Alonso, I.; Carretero, J.C. Fesulphos-palladium(II) complexes as well-defined catalysts for enantioselective ring opening of meso heterobicyclic alkenes with organozinc reagents. J. Am. Chem. Soc., 2005, 127(50), 17938-17947.
[http://dx.doi.org/10.1021/ja055692b] [PMID: 16351125]
[55]
Li, S.; Chen, H.; Yang, Q.; Yu, L.; Fan, C.; Zhou, Y.; Wang, J.; Fan, B. Iridium/NMDPP Catalyzed Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Phenolic or Naphtholic Nucleophiles. Asian J. Org. Chem., 2013, 2(6), 494.
[http://dx.doi.org/10.1002/ajoc.201300077]
[56]
Cabrera, S.; Alonso, I.; Arrayás, R.G.; Familiar, O.; Carretero, J.C. Cationic Pd II Complexes of Fesulphos Ligands: Highly Efficient Catalysts for the Enantioselective Ring Opening of Oxa- and Azabicyclic Alkenes with Dialkylzinc Reagents. Phosphorus Sulfur Silicon Relat. Elem., 2005, 180(5), 1513.
[http://dx.doi.org/10.1080/10426500590913474]
[57]
Wu, M.S.; Jeganmohan, M.; Cheng, C.H. A highly regio- and stereoselective nickel-catalyzed ring-opening reaction of alkyl- and allylzirconium reagents to 7-oxabenzonorbornadienes. J. Org. Chem., 2005, 70(23), 9545-9550.
[http://dx.doi.org/10.1021/jo051660v] [PMID: 16268631]
[58]
Lautens, M.; Fagnou, K.; Taylor, M.; Rovis, T. Rhodium-Catalysed Asymmetric Ring Opening of Oxabicyclic Alkenes with Heteroatom Nucleophiles. J. Organomet. Chem., 2001, 624(1), 259.
[http://dx.doi.org/10.1016/S0022-328X(00)00904-9]
[59]
Li, L.P.; Rayabarapu, D.K.; Nandi, M.; Cheng, C.H. Asymmetric reductive ring-opening of bicyclic olefins catalyzed by palladium and nickel complexes. Org. Lett., 2003, 5(10), 1621-1624.
[http://dx.doi.org/10.1021/ol034251z] [PMID: 12735736]
[60]
Preetz, A.; Kohrt, C.; Drexler, H.J.; Torrens, A.; Buschmann, H.; Lopez, M.G.; Heller, D. Asymmetric Ring Opening of Benzo-7-Oxabicyclo-[2.2.1]Heptadienes with Cationic Rhodium Complexes. Adv. Synth. Catal., 2010, 352(11), 2073.
[http://dx.doi.org/10.1002/adsc.201000236]
[61]
Zhang, W.; Chen, J.; Zeng, G.; Yang, F.; Xu, J.; Sun, W.; Shinde, M.V.; Fan, B. Asymmetric Ring-Opening Reactions of Aza- and Oxa-bicyclic Alkenes with Boronic Acids Using a Palladium/Zinc Co-catalytic System. J. Org. Chem., 2017, 82(5), 2641-2647.
[http://dx.doi.org/10.1021/acs.joc.6b03038] [PMID: 28112930]
[62]
Shen, G.; Chen, J.; Xu, D.; Zhang, X.; Zhou, Y.; Fan, B. Asymmetric Transfer Hydrogenation of Heterobicyclic Alkenes with Water as Hydrogen Source. Org. Lett., 2019, 21(5), 1364-1367.
[http://dx.doi.org/10.1021/acs.orglett.9b00059] [PMID: 30747537]
[63]
Yamamoto, T.; Akai, Y.; Suginome, M. Chiral palladacycle catalysts generated on a single-handed helical polymer skeleton for asymmetric arylative ring opening of 1,4-epoxy-1,4-dihydronaphthalene. Angew. Chem. Int. Ed. Engl., 2014, 53(47), 12785-12788.
[http://dx.doi.org/10.1002/anie.201407358] [PMID: 25251609]
[64]
Kong, L.; Yu, S.; Tang, G.; Wang, H.; Zhou, X.; Li, X. Cobalt(III)-Catalyzed C-C Coupling of Arenes with 7-Oxabenzonorbornadiene and 2-Vinyloxirane via C-H Activation. Org. Lett., 2016, 18(15), 3802-3805.
[http://dx.doi.org/10.1021/acs.orglett.6b01806] [PMID: 27391142]
[65]
Tan, B.H.; Yoshikai, N. Cobalt-catalyzed addition of arylzinc reagents to norbornene derivatives through 1,4-cobalt migration. Org. Lett., 2014, 16(12), 3392-3395.
[http://dx.doi.org/10.1021/ol501449j] [PMID: 24905954]
[66]
Li, Y.; Chen, J.; He, Z.; Qin, H.; Zhou, Y.; Khan, R.; Fan, B. Cobalt-Catalyzed Asymmetric Reactions of Heterobicyclic Alkenes with in Situ Generated Organozinc Halides. Org. Chem. Front., 2018, 5(7), 1108.
[http://dx.doi.org/10.1039/C7QO01064H]
[67]
Gao, P.; Foster, D.; Sipos, G.; Skelton, B.W.; Sobolev, A.N.; Dorta, R. Chiral NHC-Iridium Complexes and Their Performance in Enantioselective Intramolecular Hydroamination and Ring-Opening Amination Reactions. Organometallics, 2020, 39(4), 556.
[http://dx.doi.org/10.1021/acs.organomet.9b00770]
[68]
Tan, Y.; Yao, Y.; Yang, W.; Lin, Q.; Huang, G.; Tan, M.; Chen, S.; Chen, D.; Yang, D. Water-Promoted Palladium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with Alkoxysilanes. Adv. Synth. Catal., 2020, 362(1), 139.
[http://dx.doi.org/10.1002/adsc.201901152]
[69]
Lautens, M.; Fagnou, K. Rhodium-catalyzed asymmetric ring opening reactions of oxabicyclic alkenes: catalyst and substrate studies leading to a mechanistic working model. Proc. Natl. Acad. Sci. USA, 2004, 101(15), 5455-5460.
[http://dx.doi.org/10.1073/pnas.0307271101] [PMID: 15067134]
[70]
Chen, T.; Gan, L.; Wang, R.; Deng, Y.; Peng, F.; Lautens, M.; Shao, Z. Rhodium(I)/Zn(OTf)2 -Catalyzed Asymmetric Ring Opening/Cyclopropanation of Oxabenzonorbornadienes with Phosphorus Ylides. Angew. Chem. Int. Ed. Engl., 2019, 58(44), 15819-15823.
[http://dx.doi.org/10.1002/anie.201909596] [PMID: 31489736]
[71]
Chen, D.; Yao, Y.; Yang, W.; Lin, Q.; Li, H.; Wang, L.; Chen, S.; Tan, Y.; Yang, D. Palladium-Catalyzed syn-Stereocontrolled Ring Opening of Oxabicyclic Alkenes with Arylsulfonyl Hydrazides. J. Org. Chem., 2019, 84(19), 12481-12489.
[http://dx.doi.org/10.1021/acs.joc.9b01957] [PMID: 31512473]
[72]
Yen, A.; Pham, A.H.; Larin, E.M.; Lautens, M. Rhodium-Catalyzed Enantioselective Synthesis of Oxazinones via an Asymmetric Ring Opening-Lactonization Cascade of Oxabicyclic Alkenes. Org. Lett., 2019, 21(18), 7549-7553.
[http://dx.doi.org/10.1021/acs.orglett.9b02819] [PMID: 31539925]
[73]
Zhu, J.; Tsui, G.C.; Lautens, M. Rhodium-catalyzed enantioselective nucleophilic fluorination: ring opening of oxabicyclic alkenes. Angew. Chem. Int. Ed. Engl., 2012, 51(49), 12353-12356.
[http://dx.doi.org/10.1002/anie.201207356] [PMID: 23124934]
[74]
Lautens, M.; Hiebert, S. Scope of palladium-catalyzed alkylative ring opening. J. Am. Chem. Soc., 2004, 126(5), 1437-1447.
[http://dx.doi.org/10.1021/ja037550s] [PMID: 14759202]
[75]
Lautens, M.; Rovis, T. Scope of the Nickel Catalyzed Asymmetric Reductive Ring Opening Reaction. Synthesis of Enantiomerically Enriched Cyclohexenols. Tetrahedron, 1998, 54(7), 1107.
[http://dx.doi.org/10.1016/S0040-4020(97)10211-3]
[76]
Mo, D.L.; Chen, B.; Ding, C.H.; Dai, L.X.; Ge, G.C.; Hou, X.L. Switch of Addition and Ring-Opening Reactions of Oxabicyclic Alkenes with Terminal Alkynes by Sp2-C,P- and Sp3-C,P-Palladacycle Catalysis. Organometallics, 2013, 32(16), 4465.
[http://dx.doi.org/10.1021/om400653x]
[77]
Nakamura, M.; Matsuo, K.; Inoue, T.; Nakamura, E. Iron-catalyzed regio- and stereoselective ring opening of [2.2.1]- and [3.2.1]oxabicyclic alkenes with a Grignard reagent. Org. Lett., 2003, 5(8), 1373-1375.
[http://dx.doi.org/10.1021/ol034375b] [PMID: 12688762]
[78]
Lautens, M.; Rovis, T.; Smith, N.D.; Ostrovsky, D. Metal Catalyzed Hydrometalations and Their Applications in Synthesis. Pure Appl. Chem., 2007, 70(5), 1059.
[http://dx.doi.org/10.1351/pac199870051059]
[79]
Rayabarapu, D.K.; Cheng, C.H. New catalytic reactions of oxa- and azabicyclic alkenes. Acc. Chem. Res., 2007, 40(10), 971-983.
[http://dx.doi.org/10.1021/ar600021z] [PMID: 17591745]
[80]
Lautens, M.; Fagnou, K.; Hiebert, S. Transition metal-catalyzed enantioselective ring-opening reactions of oxabicyclic alkenes. Acc. Chem. Res., 2003, 36(1), 48-58.
[http://dx.doi.org/10.1021/ar010112a] [PMID: 12534304]
[81]
Lautens, M. Ring Opening Reactions of Oxabicyclic Compounds as a Route to Cyclic and Acyclic Compounds with Multiple Stereocenters. Synlett, 1993, 1993(3), 177.
[http://dx.doi.org/10.1055/s-1993-22393]
[82]
Madan, S.; Cheng, C.H. Nickel-catalyzed synthesis of benzocoumarins: application to the total synthesis of arnottin I. J. Org. Chem., 2006, 71(21), 8312-8315.
[http://dx.doi.org/10.1021/jo061477h] [PMID: 17025335]
[83]
Lautens, M.; Rovis, T. Selective Functionalization of 1,2-Dihydronaphthalenols Leads to a Concise, Stereoselective Synthesis of Sertraline. Tetrahedron, 1999, 55(29), 8967.
[http://dx.doi.org/10.1016/S0040-4020(99)00456-1]
[84]
Tsui, G.C.; Ninnemann, N.M.; Hosotani, A.; Lautens, M. Expedient synthesis of chiral oxazolidinone scaffolds via rhodium-catalyzed asymmetric ring-opening with sodium cyanate. Org. Lett., 2013, 15(5), 1064-1067.
[http://dx.doi.org/10.1021/ol4000668] [PMID: 23394120]
[85]
Kelebekli, L. Regio- and Stereospecific Synthesis of a New Benzoconduritol-C Derivative. J. Chem. Res., 2008, 2008(2), 104.
[http://dx.doi.org/10.3184/030823408X287104]
[86]
Hill, J.; Wicks, C.; Pounder, A.; Tam, W. Iridium-Catalyzed Ring-Opening Reactions of Unsymmetrical Oxabenzonorbornadienes with Water and Alcohol Nucleophiles. Tetrahedron, 2019, 60(34)150990
[http://dx.doi.org/10.1016/j.tetlet.2019.150990]
[87]
Allen, A.; Le Marquand, P.; Burton, R.; Villeneuve, K.; Tam, W. Rhodium-catalyzed asymmetric cyclodimerization of oxabenzonorbornadienes and azabenzonorbornadienes: scope and limitations. J. Org. Chem., 2007, 72(21), 7849-7857.
[http://dx.doi.org/10.1021/jo7012884] [PMID: 17880240]
[88]
Borowska, E.; Durka, K.; Luliński, S.; Serwatowski, J.; Woźniak, K. On the Directing Effect of Boronate Groups in the Lithiation of Boronated Thiophenes. Eur. J. Org. Chem., 2012, 2012(11), 2208.
[http://dx.doi.org/10.1002/ejoc.201101764]
[89]
Haner, J.; Jack, K.; Menard, M.L.; Howell, J.; Nagireddy, J.; Raheem, M.A.; Tam, W. Synthesis of C1-Substituted Oxabenzonorbornadienes. Synth., 2012, 44(17), 2713.
[http://dx.doi.org/10.1055/s-0032-1316686]
[90]
Raheem, M.A.; Nagireddy, J.R.; Durham, R.; Tam, W. Efficient Procedure for the Preparation of 2-Bromofuran and Its Application in the Synthesis of 2-Arylfurans. Synth. Commun., 2010, 40(14), 2138.
[http://dx.doi.org/10.1080/00397910903219534]
[91]
Haner, J.; Jack, K.; Nagireddy, J.; Raheem, M.A.; Durham, R.; Tam, W. Synthesis of 2-Substituted Furans by Iron- and Palladium-Catalyzed Coupling Reactions. Synthesis (Stuttg), 2011, 2011(5), 731.
[http://dx.doi.org/10.1055/s-0030-1259484]
[92]
Trost, B.M.; Fleming, I. Comprehensive Organic Synthesis; Pergamon Press: Oxford, UK, 1991, Vol. 5, .
[93]
Harmata, M. Advances in Cycloaddition; JAI Press: Greenwich, CT, 1999, Vol. 5, .
[94]
Pericàs, M.A.; Balsells, J.; Castro, J.; Marchueta, I.; Moyano, A.; Riera, A.; Vázquez, J.; Verdaguer, X. Toward the Understanding of the Mechanism and Enantioselectivity of the Pauson-Khand Reaction. Theoretical and Experimental Studies. Pure Appl. Chem., 2002, 74(1), 167.
[http://dx.doi.org/10.1351/pac200274010167]
[95]
Sugihara, T.; Yamaguchi, M.; Nishizawa, M. Advances in the Pauson-Khand reaction: development of reactive cobalt complexes. Chemistry, 2001, 7(8), 1589-1595.
[http://dx.doi.org/10.1002/1521-3765(20010417)7:8<1589:AID-CHEM15890>3.0.CO;2-1] [PMID: 11349898]
[96]
Brummond, K.M.; Kent, J.L. Recent Advances in the Pauson-Khand Reaction and Related. [2+2+1] Cycloadditions. Tetrahedron, 2000, 56(21), 3263.
[http://dx.doi.org/10.1016/S0040-4020(00)00148-4]
[97]
Buchwald, S.L.; Hicks, F.A. Comprehensive Asymmetric Catalysis I-III; Springer-Verlag: Berlin, 1999.
[98]
Chung, Y.; Transition Metal Alkyne Complexes, K. The Pauson–Khand Reaction. Coord. Chem. Rev., 1999, 188(1), 297.
[http://dx.doi.org/10.1016/S0010-8545(99)00032-6]
[99]
Lautens, M.; Tam, W.; Lautens, J.C.; Edwards, L.G.; Crudden, C.M.; Smith, A.C. Cobalt-Catalyzed [2π + 2π + 2π] (Homo Diels–Alder) and [2π + 2π + 4π] Cycloadditions of Bicyclo[2.2.1]Hepta-2,5-Dienes. J. Am. Chem. Soc., 1995, 117(26), 6863.
[http://dx.doi.org/10.1021/ja00131a008]
[100]
Kettles, T.J.; Cockburn, N.; Tam, W. Ruthenium-catalyzed homo Diels-Alder [2 + 2 + 2] cycloadditions of alkynyl phosphonates with bicyclo[2.2.1]hepta-2,5-diene. J. Org. Chem., 2011, 76(16), 6951-6957.
[http://dx.doi.org/10.1021/jo2010928] [PMID: 21732634]
[101]
Lautens, M.; Edwards, L.G.; Tam, W.; Lough, A.J. Nickel-Catalyzed [2π + 2π + 2π] (Homo-Diels–Alder) and [2π + 2π] Cycloadditions of Bicyclo[2.2.1]Hepta-2,5-Dienes. J. Am. Chem. Soc., 1995, 117(41), 10276.
[http://dx.doi.org/10.1021/ja00146a012]
[102]
Petko, D.; Pounder, A.; Tam, W. Ruthenium-Catalyzed [2+2+2] Bis-Homo-Diels-Alder Cycloadditions of 1,5-Cyclooctadiene with Alkynyl Phosphonates. Synth., 2019, 51(22), 4271.
[http://dx.doi.org/10.1055/s-0039-1690612]
[103]
Petko, D.; Stratton, M.; Koh, S.; Tam, W. Cationic Ruthenium-Catalyzed Bis-Homo-Diels-Alder Cycloaddition. Curr. Org. Synth., 2019, 16(5), 787-792.
[http://dx.doi.org/10.2174/1570179416666190401204448] [PMID: 31984894]
[104]
Wender, P.A.; Jenkins, T.E. Nickel-Catalyzed Intramolecular [4 + 2] Dienyne Cycloadditions: An Efficient New Method for the Synthesis of Polycycles Containing Cyclohexa-1,4-Dienes. J. Am. Chem. Soc., 1989, 111(16), 6432.
[http://dx.doi.org/10.1021/ja00198a071]
[105]
Jolly, R.S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. Novel Cyclization Reactions on Transition-Metal Templates. The Catalysis of Intramolecular [4 + 2] Cycloadditions by Low Valent Rhodium Complexes. J. Am. Chem. Soc., 1990, 112(12), 4965.
[http://dx.doi.org/10.1021/ja00168a055]
[106]
Wender, P.A.; Jenkins, T.E.; Suzuki, S. Transition Metal-Catalyzed Intramolecular [4 + 2] Diene—Allene Cycloadditions: A Convenient Synthesis of Angularly Substituted Ring Systems with Provision for Catalyst-Controlled Chemo- and Stereocomplementarity. J. Am. Chem. Soc., 1995, 117(6), 1843.
[http://dx.doi.org/10.1021/ja00111a028]
[107]
O’Mahony, D.J.R.; Belanger, D.B.; Livinghouse, T. On the Counterion Dependence of the Rhodium(I)-Catalysed [4+2] Cycloaddition - A Remarkable Accelerating Effect of the Hexafluoroantimonate Anion. Synlett, 1998, 1998(4), 443.
[http://dx.doi.org/10.1055/s-1998-1664]
[108]
Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Rhodium-Catalyzed Intermolecular. [4+2] Cycloaddition of Unactivated Substrates. Angew. Chem. Int. Ed. Engl., 1998, 37(16), 2248-2250.
[http://dx.doi.org/10.1002/(SICI)1521-3773(19980904)37:16<2248:AID-ANIE2248>3.0.CO;2-1] [PMID: 29711446]
[109]
Paik, S.J.; Son, S.U.; Chung, Y.K. Highly Efficient Intra-and Intermolecular [4 + 2] Cycloaddition Reaction Catalyzed by Rhodium Complex. Org. Lett., 1999, 1(13), 2045.
[http://dx.doi.org/10.1021/ol990169l]
[110]
Hilt, G.; Smolko, K.I. Alkynylboronic esters as efficient dienophiles in cobalt-catalyzed Diels-Alder reactions. Angew. Chem. Int. Ed. Engl., 2003, 42(24), 2795-2797.
[http://dx.doi.org/10.1002/anie.200351404] [PMID: 12820271]
[111]
Witulski, B.; Lumtscher, J.; Bergsträßer, U. First Thermal and Transition Metal Catalysed Intramolecular [4+2] Cycloaddition Reactions with N-Tethered Ynamides. Synlett, 2003, 2003(5), 708.
[http://dx.doi.org/10.1055/s-2003-38357]
[112]
Hilt, G.; Lüers, S.; Harms, K. The first broad application of alkynyl sulfides as dienophiles in cobalt(I)-catalyzed Diels-Alder reactions. J. Org. Chem., 2004, 69(3), 624-630.
[http://dx.doi.org/10.1021/jo0302915] [PMID: 14750784]
[113]
Yoo, W.J.; Allen, A.; Villeneuve, K.; Tam, W. Rhodium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides. Org. Lett., 2005, 7(26), 5853-5856.
[http://dx.doi.org/10.1021/ol052412o] [PMID: 16354083]
[114]
Tigchelaar, A.; Tam, W. Iridium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides. Beilstein J. Org. Chem., 2012, 8, 1765-1770.
[http://dx.doi.org/10.3762/bjoc.8.201] [PMID: 23209510]
[115]
Wender, P.A.; Takahashi, H.; Witulski, B. Transition Metal Catalyzed [5 + 2] Cycloadditions of Vinylcyclopropanes and Alkynes: A Homolog of the Diels-Alder Reaction for the Synthesis of Seven-Membered Rings. J. Am. Chem. Soc., 1995, 117(16), 4720.
[http://dx.doi.org/10.1021/ja00121a036]
[116]
Wender, P.A.; Rieck, H.; Fuji, M. The Transition Metal-Catalyzed Intermolecular [5+2] Cycloaddition: The Homologous Diels-Alder Reaction. J. Am. Chem. Soc., 1998, 120(42), 10976.
[http://dx.doi.org/10.1021/ja982196x]
[117]
Trost, B.M.; Shen, H.C. Constructing Tricyclic Compounds Containing a Seven-Membered Ring by Ruthenium-Catalyzed Intramolecular. [5+2] Cycloaddition. Angew. Chem. Int. Ed. Engl., 2001, 40(12), 2313-2316.
[http://dx.doi.org/10.1002/1521-3773(20010618)40:12<2313:AID-ANIE2313>3.0.CO;2-H] [PMID: 29711821]
[118]
Wender, P.A.; Williams, T.J. [(arene)Rh(cod)]+ Complexes as catalysts for [5+2] cycloaddition reactions. Angew. Chem. Int. Ed. Engl., 2002, 41(23), 4550-4553.
[http://dx.doi.org/10.1002/1521-3773(20021202)41:23<4550:AID-ANIE4550>3.0.CO;2-D] [PMID: 12458535]
[119]
Wender, P.A.; Correa, A.G.; Sato, Y.; Sun, R. Transition Metal-Catalyzed [6+2] Cycloadditions of 2-Vinylcyclobutanones and Alkenes: A New Reaction for the Synthesis of Eight-Membered Rings. J. Am. Chem. Soc., 2000, 122(32), 7815.
[http://dx.doi.org/10.1021/ja001483+]
[120]
Wender, P.A.; Ihle, N.C. Nickel-Catalyzed Intramolecular [4 + 4] Cycloadditions: A New Method for the Synthesis of Polycycles Containing Eight-Membered Rings. J. Am. Chem. Soc., 1986, 108(15), 4678.
[http://dx.doi.org/10.1021/ja00275a085]
[121]
Wender, P.A.; Nuss, J.M.; Smith, D.B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. Transition Metal Catalyzed Cycloadditions: An Intramolecular [4 + 4] Cycloaddition Strategy for the Efficient Synthesis of Dicyclopenta[a,d]Cyclooctene 5-8-5 Ring Systems. J. Org. Chem., 1997, 62(15), 4908.
[http://dx.doi.org/10.1021/jo970841x]
[122]
Lautens, M.; Klute, W.; Tam, W. Transition Metal-Mediated Cycloaddition Reactions. Chem. Rev., 1996, 96(1), 49-92.
[http://dx.doi.org/10.1021/cr950016l] [PMID: 11848744]
[123]
Burton, R.R.; Tam, W. Study on the reactivity of oxabicyclic alkenes in ruthenium-catalyzed [2+2] cycloadditions. J. Org. Chem., 2007, 72(19), 7333-7336.
[http://dx.doi.org/10.1021/jo701383d] [PMID: 17691846]
[124]
Burton, R.R.; Tam, W. Ruthenium-Catalyzed [2+2] Cycloadditions between C1-Substituted 7-Oxanorbornadienes and Alkynes. Tetrahedron Lett., 2006, 47(40), 7185.
[http://dx.doi.org/10.1016/j.tetlet.2006.07.155]
[125]
Villeneuve, K.; Tam, W. Ruthenium-Catalyzed Processes: Dual [2+2] Cycloaddition versus Cyclopropanation of Bicyclic Alkenes with Propargylic Alcohols. Organometallics, 2006, 25(4), 843.
[http://dx.doi.org/10.1021/om050780q]
[126]
Villeneuve, K.; Tam, W. Ruthenium(II)-Catalyzed Cyclization of Oxabenzonorbornenes with Propargylic Alcohols: Formation of Isochromenes. Eur. J. Org. Chem., 2006, 2006(24), 5449.
[http://dx.doi.org/10.1002/ejoc.200600836]
[127]
Trost, B.M.; Müller, T.J.J.; Martinez, J. Ruthenium-Catalyzed Synthesis of Butenolides and Pentenolides via Contra-Electronic α-Alkylation of Hydroxyalkynoates. J. Am. Chem. Soc., 1995, 117(7), 1888.
[http://dx.doi.org/10.1021/ja00112a004]
[128]
Trost, B.M.; Müller, T.J.J. Butenolide Synthesis Based upon a Contra-Electronic Addition in a Ruthenium-Catalyzed Alder Ene Reaction. Synthesis and Absolute Configuration of. (+)- Ancepsenolide. J. Am. Chem. Soc., 1994, 116(11), 4985.
[http://dx.doi.org/10.1021/ja00090a053]
[129]
Tenaglia, A.; Marc, S.; Giordano, L.; De Riggi, I. Ruthenium-catalyzed coupling of oxabenzonorbornadienes with alkynes bearing a propargylic oxygen atom: access to stereodefined benzonorcaradienes. Angew. Chem. Int. Ed. Engl., 2011, 50(39), 9062-9065.
[http://dx.doi.org/10.1002/anie.201104589] [PMID: 21858905]
[130]
Allen, A.; Villeneuve, K.; Cockburn, N.; Fatila, E.; Riddell, N.; Tam, W. Alkynyl Halides in Ruthenium(II)-Catalyzed. [2+2] Cycloadditions of Bicyclic Alkenes. Eur. J. Org. Chem., 2008, 2008(24), 4178.
[http://dx.doi.org/10.1002/ejoc.200800424]
[131]
Rayabarapu, D.K.; Sambaiah, T.; Cheng, C.H. Nickel-Catalyzed Highly Regio- and Stereoselective Cyclization of Oxanorbornenes with Alkyl Propiolates: A Novel Method for the Synthesis of Benzocoumarin Derivatives. Angew. Chem. Int. Ed. Engl., 2001, 40(7), 1286-1288.
[http://dx.doi.org/10.1002/1521-3773(20010401)40:7<1286:AID-ANIE1286>3.0.CO;2-I] [PMID: 11301453]
[132]
Yang, Q.; Yu, L.; Xu, J.; Li, S.; Liu, S.; Chen, H.; Zhou, Y.; Wang, L.; Fan, B. Kinetic Resolution of C1-Substituted Oxabenzonorbornadienes by Ir-Catalyzed Asymmetric [2+2] Cycloaddition Reactions with Arylacetylenes. Tetrahedron Asymmetry, 2014, 25(13–14), 957.
[http://dx.doi.org/10.1016/j.tetasy.2014.06.007]
[133]
Nagireddy, J.R.; Carlson, E.; Tam, W. 1,3-Dipolar Cycloaddition of Nitrile Oxides with C1-Substituted 7-Oxabenzonorbornadienes. Can. J. Chem., 2014, 92(11), 1053.
[http://dx.doi.org/10.1139/cjc-2014-0274]
[134]
Chen, W.; Yang, W.; Wu, R.; Yang, D. Water-Promoted Synthesis of Fused Bicyclic Triazolines and Naphthols from Oxa(Aza)Bicyclic Alkenes and Transformation: Via a Novel Ring-Opening/Rearrangement Reaction. Green Chem., 2018, 20(11), 2512.
[http://dx.doi.org/10.1039/C7GC03772D]
[135]
Chen, S.; Yao, Y.; Yang, W.; Lin, Q.; Wang, L.; Li, H.; Chen, D.; Tan, Y.; Yang, D. Three-Component Cycloaddition To Synthesize Aziridines and 1,2,3-Triazolines. J. Org. Chem., 2019, 84(18), 11863-11872.
[http://dx.doi.org/10.1021/acs.joc.9b01713] [PMID: 31469559]
[136]
Wolthuis, E.; Bossenbroek, B.; DeWall, G.; Geels, E.; Leegwater, A. Reactions of Methyl-Substituted 1,4-Epoxy-1,4-Dihydronaphthalenes. J. Org. Chem., 1963, 28(1), 148.
[http://dx.doi.org/10.1021/jo01036a034]
[137]
Batt, D.G.; Jones, D.G.; La Greca, S. Regioselectivity in the Acid-Catalyzed Isomerization of 2-Substituted 1,4-Dihydro-1,4-Epoxynaphthalenes. J. Org. Chem., 1991, 56(23), 6704.
[http://dx.doi.org/10.1021/jo00023a041]
[138]
Peng, F.; Fan, B.; Shao, Z.; Pu, X.; Li, P.; Zhang, H. Cu(OTf)2-Catalyzed Isomerization of 7-Oxabicyclic Alkenes: A Practical Route to the Synthesis of 1-Naphthol Derivatives. Synthesis (Stuttg), 2008, 2008(19), 3043.
[http://dx.doi.org/10.1055/s-2008-1067268]
[139]
Zhou, Y.; Liu, S.; Chen, H.; Chen, J.; Sun, W.; Li, S.; Yang, Q.; Fan, B. AgOTf-Catalyzed Tandem Reaction of Oxabenzonorbornadienes with Arylacetylenes. Chin. J. Chem., 2015, 33(10), 1115.
[http://dx.doi.org/10.1002/cjoc.201500392]
[140]
Dang, T.T.; Boeck, F.; Hintermann, L. Hidden Brønsted acid catalysis: pathways of accidental or deliberate generation of triflic acid from metal triflates. J. Org. Chem., 2011, 76(22), 9353-9361.
[http://dx.doi.org/10.1021/jo201631x] [PMID: 22010906]
[141]
Villeneuve, K.; Tam, W. Ruthenium-catalyzed isomerization of oxa/azabicyclic alkenes: an expedient route for the synthesis of 1,2-naphthalene oxides and imines. J. Am. Chem. Soc., 2006, 128(11), 3514-3515.
[http://dx.doi.org/10.1021/ja058621l] [PMID: 16536513]
[142]
Brandt, P.; Jia, Z.S.; Thibblin, A. Kinetic and thermodynamic stability of naphthalene oxide and related compounds. A comparative microcalorimetric and computational (DFT) study. J. Org. Chem., 2002, 67(22), 7676-7682.
[http://dx.doi.org/10.1021/jo025953p] [PMID: 12398489]
[143]
Rao, S.N.; O’Ferrall, R.A.M.; Kelly, S.C.; Boyd, D.R.; Agarwal, R. Acid-Catalyzed Aromatizations of Arene Oxides and Arene Hydrates: Are Arene Oxides Homoaromatic? J. Am. Chem. Soc., 1993, 115(13), 5458.
[http://dx.doi.org/10.1021/ja00066a015]
[144]
Ballantine, M.; Menard, M.L.; Tam, W. Isomerization of 7-oxabenzonorbornadienes into naphthols catalyzed by [RuCl(2)(CO)(3)](2). J. Org. Chem., 2009, 74(19), 7570-7573.
[http://dx.doi.org/10.1021/jo901504n] [PMID: 19725525]
[145]
Zou, L.; Sun, W.; Khan, R.; Lv, H.; Yang, Y.; Xu, J.; Zhan, Y.; Fan, B. Palladium Catalyzed Tandem Reaction of Oxabenzonorbornadienes with Anhydrides. Eur. J. Org. Chem., 2019, 2019(4), 746.
[http://dx.doi.org/10.1002/ejoc.201801372]
[146]
Shih, H.T.; Shih, H.H.; Cheng, C.H. Synthesis of biaryls via unusual deoxygenative dimerization of 1,4-epoxy-1,4-dihydroarenes catalyzed by palladium complexes. Org. Lett., 2001, 3(6), 811-814.
[http://dx.doi.org/10.1021/ol0069204] [PMID: 11263888]
[147]
Nishimura, T.; Kawamoto, T.; Sasaki, K.; Tsurumaki, E.; Hayashi, T. Rhodium-catalyzed asymmetric cyclodimerization of oxa- and azabicyclic alkenes. J. Am. Chem. Soc., 2007, 129(6), 1492-1493.
[http://dx.doi.org/10.1021/ja068488c] [PMID: 17283982]
[148]
Butler, M.S.; Capon, R.J. Trunculin-F and Contrunculin-A and -B: Novel Oxygenated Norterpenes from a Southern Australian Marine Sponge, Latrunculia Conulosa. Aust. J. Chem., 1993, 46(9), 1363.
[http://dx.doi.org/10.1071/CH9931363]
[149]
Corey, E.J. The Stereochemistry of Santonin, β-Santonin and Artemisin. J. Am. Chem. Soc., 1955, 77(4), 1044.
[http://dx.doi.org/10.1021/ja01609a076]
[150]
Hill, J.; Tam, W. Palladium/Lewis Acid Cocatalyzed Ring-Opening Reactions of Unsymmetrical Oxabenzonobornadienes with Oximes. J. Org. Chem., 2019, 84(12), 8309-8314.
[http://dx.doi.org/10.1021/acs.joc.9b01094] [PMID: 31192590]
[151]
Sakae, R.; Hirano, K.; Satoh, T.; Miura, M. Copper-catalyzed stereoselective aminoboration of bicyclic alkenes. Angew. Chem. Int. Ed. Engl., 2015, 54(2), 613-617.
[PMID: 25404258]
[152]
Nagamoto, M.; Nishimura, T. Stereoselective hydroacylation of bicyclic alkenes with 2-hydroxybenzaldehydes catalyzed by hydroxoiridium/diene complexes. Chem. Commun. (Camb.), 2015, 51(72), 13791-13794.
[http://dx.doi.org/10.1039/C5CC05432J] [PMID: 26235305]
[153]
González-Rodríguez, C.; Willis, M.C. Rhodium-Catalyzed Enantioselective Intermolecular Hydroacylation Reactions. Pure Appl. Chem., 2011, 83(3), 577.
[http://dx.doi.org/10.1351/PAC-CON-10-09-23]
[154]
Stemmler, R.T.; Bolm, C. An Unprecedented Rhodium-Catalyzed Asymmetric Intermolecular Hydroacylation Reaction with Salicylaldehydes. Adv. Synth. Catal., 2007, 349(7), 1185.
[http://dx.doi.org/10.1002/adsc.200600583]
[155]
Ito, S.; Itoh, T.; Nakamura, M. Diastereoselective carbometalation of oxa- and azabicyclic alkenes under iron catalysis. Angew. Chem. Int. Ed. Engl., 2011, 50(2), 454-457.
[http://dx.doi.org/10.1002/anie.201006180] [PMID: 21154797]
[156]
Li, S.; Yang, Q.; Bian, Z.; Wang, J. Rhodium-Catalyzed Enantioselective Hydroselenation of Heterobicyclic Alkenes. Org. Lett., 2020, 22(7), 2781-2785.
[http://dx.doi.org/10.1021/acs.orglett.0c00762] [PMID: 32195590]
[157]
Lautens, M.; Fagnou, K.; Yang, D. Rhodium-catalyzed asymmetric ring opening reactions of oxabicyclic alkenes: application of halide effects in the development of a general process. J. Am. Chem. Soc., 2003, 125(48), 14884-14892.
[http://dx.doi.org/10.1021/ja034845x] [PMID: 14640665]
[158]
Bos, P.H.; Rudolph, A.; Pérez, M.; Fañanás-Mastral, M.; Harutyunyan, S.R.; Feringa, B.L. Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with organolithium reagents. Chem. Commun. (Camb.), 2012, 48(12), 1748-1750.
[http://dx.doi.org/10.1039/c2cc16855c] [PMID: 22215200]
[159]
Ladjel, C.; Fuchs, N.; Zhao, J.; Bernardinelli, G.; Alexakis, A. New Bifunctional Substrates for Copper‐Catalyzed Asymmetric Conjugate Addition Reactions with Trialkylaluminium. Eur. J. Org. Chem., 2009, 2009(29), 4949.
[http://dx.doi.org/10.1002/ejoc.200900662]
[160]
Yang, D.; Hu, P.; Long, Y.; Wu, Y.; Zeng, H.; Wang, H.; Zuo, X. Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles. Beilstein J. Org. Chem., 2009, 5(53), 53.
[http://dx.doi.org/10.3762/bjoc.5.53] [PMID: 20126558]
[161]
Yang, D.; Long, Y.; Zhang, J.; Zeng, H.; Wang, S.; Li, C. Iridium-Catalyzed Asymmetric Ring-Opening Reactions of Oxabenzonorbornadienes with Amine Nucleophiles. Organometallics, 2010, 29(16), 3477.
[http://dx.doi.org/10.1021/om100384q]
[162]
Long, Y.; Li, X.; Pan, X.; Ding, D.; Xu, X.; Zuo, X.; Yang, D.; Wang, S.; Li, C. Iridium-Catalyzed Asymmetric Ring-Opening of Oxabicyclic Alkenes with Carboxylic Acids. Catal. Lett., 2014, 144(3), 419.
[http://dx.doi.org/10.1007/s10562-013-1136-x]
[163]
Mannathan, S.; Cheng, C.H. Nickel-Catalyzed Regio- and Stereoselective Reductive Coupling of Oxa- and Azabicyclic Alkenes with Enones and Electron-Rich Alkynes. Adv. Synth. Catal., 2014, 356(10), 2239.
[http://dx.doi.org/10.1002/adsc.201300910]
[164]
Shukla, P.; Sharma, A.; Pallavi, B.; Cheng, C.H. Nickel-Catalyzed Reductive Heck Type Coupling of Saturated Alkyl Halides with Acrylates and Oxabenzonorbornadiene. Tetrahedron, 2015, 71(15), 2260.
[http://dx.doi.org/10.1016/j.tet.2015.02.067]
[165]
Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. Nickel-Catalyzed Hydroalumination of Oxabicyclic Alkenes. Ligand Effects on the Regio- and Enantioselectivity. J. Am. Chem. Soc., 1995, 117(1), 532.
[http://dx.doi.org/10.1021/ja00106a062]
[166]
Koh, S.; Pounder, A.; Brown, E.; Tam, W. Intramolecular Nickel-Catalyzed Ring-Opening Reactions of Oxabenzonorbornadienes with C1-Tethered Aryl Halides: An Improvement of Method. Eur. J. Org. Chem., 2020, 2020(29), 4558.
[http://dx.doi.org/10.1002/ejoc.202000672]
[167]
Li, Y.; Yang, W.; Cheng, G.; Yang, D. Palladium-catalyzed syn-stereocontrolled ring-opening of oxabicyclic alkenes with sodium arylsulfinates. J. Org. Chem., 2016, 81(11), 4744-4750.
[http://dx.doi.org/10.1021/acs.joc.6b00667] [PMID: 27150019]
[168]
Chen, H.; Li, S.; Xu, J.; Yang, Q.; Liu, S.; Zhou, Y.; Huang, C.; Fan, B. Palladium-Catalyzed Ring-Opening Reaction of Oxa/Azabenzonorbornadienes with Aryl Acetylenes. Acta Chimi. Sin., 2013, 71(9), 1243.
[169]
Parthasarathy, K.; Jeganmohan, M.; Cheng, C.H. Palladium-catalyzed multistep reactions involving ring closure of 2-iodophenoxyallenes and ring opening of bicyclic alkenes. Org. Lett., 2006, 8(4), 621-623.
[http://dx.doi.org/10.1021/ol0527936] [PMID: 16468726]
[170]
Li, M.; Yan, X.X.; Hong, W.; Zhu, X.Z.; Cao, B.X.; Sun, J.; Hou, X.L. Palladium-catalyzed enantioselective ring opening of oxabicyclic alkenes with organozinc halides. Org. Lett., 2004, 6(16), 2833-2835.
[http://dx.doi.org/10.1021/ol048816i] [PMID: 15281781]
[171]
Lautens, M.; Renaud, J.L.; Hiebert, S. Palladium-Catalyzed Enantioselective Alkylative Ring Opening. J. Am. Chem. Soc., 2000, 122(8), 1804.
[http://dx.doi.org/10.1021/ja993427i]
[172]
Li, S.; Xu, J.; Fan, B.; Lu, Z.; Zeng, C.; Bian, Z.; Zhou, Y.; Wang, J. Palladium/Zinc Co-Catalyzed syn-Stereoselectively Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Phenols. Chemistry, 2015, 21(25), 9003-9007.
[http://dx.doi.org/10.1002/chem.201500816] [PMID: 25907319]
[173]
Koh, S.; Pounder, A.; Brown, E.; Tam, W. Intramolecular Palladium-Catalyzed Ring Opening of Oxabenzonorbornadienes with C1-Tethered Aryl Halides. Org. Lett., 2020, 22(9), 3433-3437.
[http://dx.doi.org/10.1021/acs.orglett.0c00900] [PMID: 32294386]
[174]
Pan, X.; Huang, G.; Long, Y.; Zuo, X.; Xu, X.; Gu, F.; Yang, D. Platinum(II)-catalyzed asymmetric ring-opening addition of arylboronic acids to oxabenzonorbornadienes. J. Org. Chem., 2014, 79(1), 187-196.
[http://dx.doi.org/10.1021/jo402386k] [PMID: 24274880]
[175]
Long, Y.; Jiang, H.; Zou, Z.; Chen, K.; Fang, Y. Platinum-Catalyzed Asymmetric Ring-Opening Reaction of Oxabenzonorbornadiene with Terminal Alkynesa. Chin. J. Chem., 2014, 32(7), 613.
[http://dx.doi.org/10.1002/cjoc.201400174]
[176]
Yang, D.; Liang, N. Platinum-catalyzed anti-stereocontrolled ring-opening of oxabicyclic alkenes with Grignard reagents. Org. Biomol. Chem., 2014, 12(13), 2080-2086.
[http://dx.doi.org/10.1039/c3ob42199f] [PMID: 24549179]
[177]
Lautens, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with organoboronic acids. Org. Lett., 2002, 4(8), 1311-1314.
[http://dx.doi.org/10.1021/ol0256062] [PMID: 11950350]
[178]
Chen, J.; Zou, L.; Zeng, C.; Zhou, Y.; Fan, B. Rhodium-Catalyzed Asymmetric Arylative Ring-Opening Reactions of Heterobicyclic Alkenes with Anilines. Org. Lett., 2018, 20(5), 1283-1286.
[http://dx.doi.org/10.1021/acs.orglett.7b03941] [PMID: 29469577]
[179]
Yang, T.; Zhang, T.; Yang, S.; Chen, S.; Li, X. Rhodium(III)-catalyzed coupling of N-sulfonyl 2-aminobenzaldehydes with oxygenated allylic olefins through C-H activation. Org. Biomol. Chem., 2014, 12(25), 4290-4294.
[http://dx.doi.org/10.1039/C4OB00704B] [PMID: 24838825]
[180]
Tsui, G.C.; Lautens, M. Rhodium(I)-catalyzed domino asymmetric ring opening/enantioselective isomerization of oxabicyclic alkenes with water. Angew. Chem. Int. Ed. Engl., 2012, 51(22), 5400-5404.
[http://dx.doi.org/10.1002/anie.201200390] [PMID: 22511539]
[181]
Millward, D.B.; Sammis, G.; Waymouth, R.M. Ring-opening reactions of oxabicyclic alkene compounds: enantioselective hydride and ethyl additions catalyzed by group 4 metals. J. Org. Chem., 2000, 65(13), 3902-3909.
[http://dx.doi.org/10.1021/jo991429f] [PMID: 10866606]
[182]
Snyder, S.E.; Kamal, A.; Gayatri, L.; Kim, K.; Guo, Y.; Sulikowski, G.A.; Perrone, R.; Lautens, M.; Fagnou, K.; Rovis, T. Rhodium-Catalyzed Asymmetric Ring Opening of Oxabicyclic Alkenes with Phenols. Anal. Profiles Drug Subst. Excipients, 1996, 2(12), 1677.
[183]
Meng, L.; Yang, W.; Pan, X.; Tao, M.; Cheng, G.; Wang, S.; Zeng, H.; Long, Y.; Yang, D. Platinum-catalyzed asymmetric ring-opening reactions of oxabenzonorbornadienes with phenols. J. Org. Chem., 2015, 80(5), 2503-2512.
[http://dx.doi.org/10.1021/acs.joc.5b00065] [PMID: 25679332]
[184]
Xu, X.; Chen, J.; He, Z.; Zhou, Y.; Fan, B. Rhodium-catalyzed asymmetric ring opening reaction of oxabenzonorbornadienes with amines using ZnI2 as the activator. Org. Biomol. Chem., 2016, 14(8), 2480-2486.
[http://dx.doi.org/10.1039/C5OB02331A] [PMID: 26814591]
[185]
Yu, L.; Zhou, Y.; Xu, X.; Li, S.; Xu, J.; Fan, B.; Lin, C.; Bian, Z.; Chan, A.S.C. Asymmetric Ring Opening Reaction of Oxabenzonorbornadienes with Amines Promoted by Iridium/NMDPP Complex. Tetrahedron Lett., 2014, 55(46), 6315.
[http://dx.doi.org/10.1016/j.tetlet.2014.09.089]
[186]
Lautens, M.; Fagnou, K. Rhodium-Catalysed Asymmetric Ring Opening Reactions with Carboxylate Nucleophiles. Tetrahedron, 2001, 57(24), 5067.
[http://dx.doi.org/10.1016/S0040-4020(01)00351-9]
[187]
He, X.; Chen, J.; Xu, X.; Yang, F.; Gu, C.; Zhou, Y.; Fan, B. Rhodium/Zinc Co-Catalyzed Asymmetric Ring Opening Reactions of Oxabenzonorbornadienes with Carboxylic Acids. Tetrahedron Asymmetry, 2017, 28(1), 62.
[http://dx.doi.org/10.1016/j.tetasy.2016.11.004]
[188]
Shen, G.; Khan, R.; Yang, F.; Yang, Y.; Pu, D.; Gao, Y.; Zhan, Y.; Luo, Y.; Fan, B. Pd/Zn Co-Catalyzed Asymmetric Ring-Opening Reactions of Aza/Oxabicyclic Alkenes with Oximes. Asian J. Org. Chem., 2019, 8(1), 97.
[http://dx.doi.org/10.1002/ajoc.201800569]
[189]
Leong, P.; Lautens, M. Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with sulfur nucleophiles. J. Org. Chem., 2004, 69(6), 2194-2196.
[http://dx.doi.org/10.1021/jo035730e] [PMID: 15058972]
[190]
Cheng, G.; Yang, W.; Li, Y.; Yang, D. Iridium/Copper Co-catalyzed Anti-Stereoselective Ring Opening of Oxabenzonorbornadienes with Grignard Reagents. J. Org. Chem., 2016, 81(17), 7817-7823.
[http://dx.doi.org/10.1021/acs.joc.6b01479] [PMID: 27455165]
[191]
Millet, R.; Bernardez, T.; Palais, L.; Alexakis, A. Copper-catalyzed desymmetrization of oxabenzonorbornadienes with aluminum reagents. Tetrahedron Lett., 2009, 50(26), 3474.
[http://dx.doi.org/10.1016/j.tetlet.2009.02.219]
[192]
Lautens, M.; Dockendorff, C. Palladium(II) catalyst systems for the addition of boronic acids to bicyclic alkenes: new scope and reactivity. Org. Lett., 2003, 5(20), 3695-3698.
[http://dx.doi.org/10.1021/ol035369i] [PMID: 14507207]
[193]
Huang, X.J.; Mo, D.L.; Ding, C.H.; Hou, X.L. Chiral P-Containing Palladacycle-Catalyzed Asymmetric Ring-Opening Reactions of Oxabicyclic Alkenes with Alkenyl Boronic Acids. Synlett, 2011, 2011(7), 943.
[http://dx.doi.org/10.1055/s-0030-1259716]
[194]
Zeng, Z.; Yang, D.; Long, Y.; Pan, X.; Huang, G.; Zuo, X.; Zhou, W. Nickel-catalyzed asymmetric ring opening of oxabenzonorbornadienes with arylboronic acids. J. Org. Chem., 2014, 79(11), 5249-5257.
[http://dx.doi.org/10.1021/jo500821m] [PMID: 24823677]
[195]
Lautens, M.; Di Felice, C.; Huboux, A. Ring-Opening Reactions of an Oxabicyclic Compound with Cuprates. Tetrahedron Lett., 1989, 30(49), 6817.
[http://dx.doi.org/10.1016/S0040-4039(01)93360-X]
[196]
Caple, R.; Chen, G.M-S.; Nelson, J.D. The Addition of Butyllithiums to Benzonorbornadiene and 1,4-Dihydronaphthalene 1,4-Endo-Oxide. J. Org. Chem., 1971, 36(19), 2874.
[http://dx.doi.org/10.1021/jo00818a032]
[197]
Priego, J.; Mancheno, O.G.; Cabrera, S.; Arrayas, R.G.; Llamas, T.; Carretero, J.C. 1-Phosphino-2-Sulfenylferrocenes: Efficient Ligands in Enantioselective Palladium-Catalyzed Allylic Substitutions and Ring Opening of 7-Oxabenzonorbornadienes. Chem. Commun. (Camb.), 2002, 0(21), 2512.
[http://dx.doi.org/10.1039/B207344G]
[198]
Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L.A.; Minnaard, A.J.; Feringa, B.L. Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: remarkable reversal of stereocontrol. Org. Lett., 2002, 4(16), 2703-2705.
[http://dx.doi.org/10.1021/ol026220u] [PMID: 12153214]
[199]
Arrayás, R.G.; Cabrera, S.; Carretero, J.C. Copper-Catalyzed Ring-Opening of Heterobicyclic Alkenes with Grignard Reagents: Remarkably High Anti-Stereocontrol. Synthesis (Stuttg), 2006, 2006(7), 1205.
[http://dx.doi.org/10.1055/s-2006-926379]
[200]
Zhang, W.; Zhu, S.F.; Qiao, X.C.; Zhou, Q.L. Highly enantioselective copper-catalyzed ring opening of oxabicyclic alkenes with Grignard reagents. Chem. Asian J., 2008, 3(12), 2105-2111.
[http://dx.doi.org/10.1002/asia.200800159] [PMID: 18823061]
[201]
Millet, R.; Gremaud, L.; Bernardez, T.; Palais, L.; Alexakis, A. Copper-Catalyzed Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Grignard and Aluminum Reagents. Synthesis (Stuttg), 2009, 2009(12), 2101.
[http://dx.doi.org/10.1055/s-0029-1216838]
[202]
Yang, D.; Long, Y.; Wang, H.; Zhang, Z. Iridium-catalyzed asymmetric ring-opening reactions of N-Boc-azabenzonorbornadiene with secondary amine nucleophiles. Org. Lett., 2008, 10(21), 4723-4726.
[http://dx.doi.org/10.1021/ol801768e] [PMID: 18834138]
[203]
Yang, X.; Yang, W.; Yao, Y.; Deng, Y.; Zuo, X.; Yang, D. Water-Promoted Ir-Catalyzed Ring-Opening of Oxa(aza)benzonorbornadienes with Fluoroalkylamines. J. Org. Chem., 2018, 83(17), 10097-10106.
[http://dx.doi.org/10.1021/acs.joc.8b01396] [PMID: 30040416]
[204]
Lautens, M.; Fagnou, K. Effects of halide ligands and protic additives on enantioselectivity and reactivity in rhodium-catalyzed asymmetric ring-opening reactions. J. Am. Chem. Soc., 2001, 123(29), 7170-7171.
[http://dx.doi.org/10.1021/ja010262g] [PMID: 11459502]
[205]
Yang, X.; Yang, W.; Yao, Y.; Deng, Y.; Yang, D. Ir-Catalyzed Ring-Opening of Oxa(Aza)Benzonorbornadienes with Water or Alcohols. Org. Chem. Front., 2019, 6(8), 1151.
[http://dx.doi.org/10.1039/C8QO01403E]
[206]
Deng, Y.; Yang, W.; Yao, Y.; Yang, X.; Zuo, X.; Yang, D. Nickel-catalyzed syn-stereocontrolled ring-opening of oxa- and azabicyclic alkenes with dialkylzinc reagents. Org. Biomol. Chem., 2019, 17(3), 703-711.
[http://dx.doi.org/10.1039/C8OB02864H] [PMID: 30608102]
[207]
Rayabarapu, D.K.; Shukla, P.; Cheng, C.H. Cyclization of oxa-bicyclic alkenes with β-iodo-(Z)-propenoates and o-iodobenzoate catalyzed by nickel complexes: a simple efficient route to annulated coumarins. Org. Lett., 2003, 5(25), 4903-4906.
[http://dx.doi.org/10.1021/ol036027f] [PMID: 14653703]
[208]
Luo, Y.; Gutiérrez-Bonet, Á.; Matsui, J.K.; Rotella, M.E.; Dykstra, R.; Gutierrez, O.; Molander, G.A. Oxa- And Azabenzonorbornadienes as Electrophilic Partners under Photoredox/Nickel Dual Catalysis. ACS Catal., 2019, 9(9), 8835.
[http://dx.doi.org/10.1021/acscatal.9b02458]
[209]
Diallo, A.G.; Roy, D.; Gaillard, S.; Lautens, M.; Renaud, J.L. Aminomethylation of Oxabenzonorbornadienes via the Merger of Photoredox and Nickel Catalysis. Org. Lett., 2020, 22(6), 2442-2447.
[http://dx.doi.org/10.1021/acs.orglett.0c00593] [PMID: 32118455]
[210]
Duan, J.P.; Cheng, C.H. Palladium-Catalyzed Reductive Couplings of Organic Halides with 7-Heteroatom Norbornadienes. New Synthetic Methods for Substituted Aryls and Cis- 1,2-Dihydro-1-Naphthyl Alcohols and Carbamates. Organometallics, 1995, 14(4), 1608.
[http://dx.doi.org/10.1021/om00004a014]
[211]
Raheem, M.A.; Edmunds, M.; Tam, W. Regioselective Palladium-Catalyzed Ring-Opening Reactions of C 1 -Substituted Oxabenzonorbornadienes. Can. J. Chem., 2014, 92(9), 888.
[http://dx.doi.org/10.1139/cjc-2014-0217]
[212]
Faiz Norrrahim, M.N.; Idayu Abdul Razak, M.A.; Ahmad Shah, N.A.; Kasim, H.; Wan Yusoff, W.Y.; Halim, N.A.; Mohd Nor, S.A.; Jamal, S.H.; Ong, K.K.; Zin Wan Yunus, W.M. Recent developments on oximes to improve the blood brain barrier penetration for the treatment of organophosphorus poisoning: A Review. RSC Advances, 2020, 10(8), 4465.
[http://dx.doi.org/10.1039/C9RA08599H]
[213]
Murakami, M.; Igawa, H. Rhodium-catalysed addition of arylboronic acids to oxabenzonorbornadienes. Chem. Commun. (Camb.), 2002, 4(4), 390-391.
[http://dx.doi.org/10.1039/b108808d] [PMID: 12120089]
[214]
Edmunds, M.; Menard, M.L.; Tam, W. Study on the Regioselectivity of Rhodium-Catalyzed Ring Opening Reactions of C 1-Substituted 7-Oxabenzonorbornadienes with Boronic Acids. Synth. Commun., 2015, 45(4), 458.
[http://dx.doi.org/10.1080/00397911.2014.965330]
[215]
Jack, K.; Fatila, E.; Hillis, C.; Tam, W. Ruthenium-Catalyzed Nucleophilic Ring-Opening Reactions of 7-Oxabenzonorbornadienes with Methanol. Synth. Commun., 2013, 43(8), 1811.
[http://dx.doi.org/10.1080/00397911.2011.626140]

Rights & Permissions Print Cite
Article Metrics
23
1
© 2024 Bentham Science Publishers | Privacy Policy