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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Trifunctionalized Allenes. Part IV. Cyclization Reactions of 4-Phosphorylated 5-Hydroxyhexa-2,3-dienoates

Author(s): Ismail E. Ismailov, Ivaylo K. Ivanov and Valerij Ch. Christov*

Volume 17, Issue 9, 2020

Page: [726 - 733] Pages: 8

DOI: 10.2174/1570178617666200225104238

Price: $65

Abstract

This manuscript focuses on the reactions of 4-phosphorylated 5-hydroxyhexa-2,3-dienoates with protected or unprotected hydroxy groups involving 5-endo-trig cyclizations. Reactions with electrophiles result in mixtures of the 2,5-dihydro-1,2-oxaphosphole-5-carboxylates and the 5-phosphorylfuran- 2(5H)-ones by competitive electrophilic cyclization due to the neighboring phosphonate (phosphine oxide) and the carboxylate groups participation. 4-Phosphorylated 5-hydroxyhexa-2,3-dienoates were smoothly transformed into the corresponding 4-phosphoryl-2,5-dihydrofuran-2-carboxylates by using 5 mol % of a silver salt as a catalyst in the 5-endo-trig cycloisomerization reaction.

Keywords: 4-phosphorylated 5-hydroxyhexa-2, 3-dienoates, electrophilic cyclization, 2, 5-dihydro-1, 2-oxaphospholes, furan- 2(5H)-ones, silver-catalyzed cycloisomerization, 2, 5-dihydrofurans.

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[1]
(a)Schuster, H.F.; Coppola, G.M. Allenes in Organic Synthesis, Wiley: New York, 1984.
(b)Krause, N.; Hashmi, A.S.K., Eds.; Modern Allene Chemistry; Wiley-VCH: Weinheim, 2004.
[http://dx.doi.org/10.1002/9783527619573]
(c)Brasholz, M.; Reissig, H-U. Zimmer, R. Acc. Chem. Res., 2009, 42, 45-56.
[http://dx.doi.org/10.1021/ar800011h]
(d)Yu, S.; Ma, S. Angew. Chem. Int. Ed., 2012, 51, 3074-3112.
[http://dx.doi.org/10.1002/anie.201101460]
[2]
Hoffmann-Röder, A.; Krause, N. Angew. Chem. Int. Ed., 2004, 43, 1196-1216.
[http://dx.doi.org/10.1002/anie.200300628]
[3]
(a)Yu, F.; Lian, X.; Ma, S. Org. Lett., 2007, 9, 1703-1706.
[http://dx.doi.org/10.1021/ol0703478]
(b)Li, P.; Liu, Z.J.; Liu, J.T. Tetrahedron, 2010, 66, 9729-9732.
[http://dx.doi.org/10.1016/j.tet.2010.10.040]
(c)Xin, N.; Ma, S. Eur. J. Org. Chem., 2012, 3806-3817.
[http://dx.doi.org/10.1002/ejoc.201200228]
(d)Fourgeaud, P.; Volle, J.N.; Vors, J.P.; Bekro, Y.A.; Pirat, J.L.; Virieux, D. Tetrahedron, 2016, 72, 7912-7925.
[http://dx.doi.org/10.1016/j.tet.2016.10.011]
(e)Essid, I.; Laborde, C.; Legros, F.; Sevrain, N.; Touil, S.; Rolland, M.; Ayad, T.; Volle, J.N.; Pirat, J.L.; Virieux, D. Org. Lett., 2017, 19, 1882-1885.
[http://dx.doi.org/10.1021/acs.orglett.7b00648]
[4]
(a)Angelov, C.M. Zh. Obshch. Khim., 1980, 50, 2448-2452.
(b)Angelov, C.M.; Stoianov, N.M.; Ionin, B.I. Zh. Obshch. Khim., 1982, 52, 178-181.
(c)Angelov, C.M.; Christov, C.Z. Synthesis, 1984, 664-667.
[http://dx.doi.org/10.1055/s-1984-30926]
(d)Yu, F.; Lian, X.; Zhao, J.; Yu, Y.; Ma, S. J. Org. Chem., 2009, 74, 1130-1134.
[http://dx.doi.org/10.1021/jo802051r]
(e)Angelov, C.M. Phosphorus. Sulfur Relat. Elem., 1983, 15, 177-193.
(f)Khusainova, N.G.; Pudovik, A.N. Russ. Chem. Rev., 1987, 56, 564-578.
[http://dx.doi.org/10.1070/RC1987v056n06ABEH003290]
(g)Alabugin, I.V.; Brel, V.K. Russ. Chem. Rev., 1997, 66, 205-224.
[http://dx.doi.org/10.1070/RC1997v066n03ABEH000262]
(h)Ma, S. Acc. Chem. Res., 2009, 42, 1679-1688.
[http://dx.doi.org/10.1021/ar900153r]
(i) Brel, V.K. Heteroatom Chem., 2006, 17, 547-556.
[http://dx.doi.org/10.1002/hc.20275]
[5]
(a)Angelov, C.M.; Christov, C.Z.; Ionin, B.I. Zh. Obshch. Khim., 1982, 52, 264-267.
(b)Khusainova, N.G.; Naumova, L.V.; Berdnikov, E.A.; Pudovik, A.N. Zh. Obshch. Khim., 1982, 52, 1040-1046.
(c)Enchev, D.D.; Angelov, C.M.; Krawchik, E.; Skowronska, A.; Michalski, J. Phosphorus Sulfur Silicon Relat. Elem., 1991, 57, 249-253.
[http://dx.doi.org/10.1080/10426509108038856]
[6]
(a)Rao, Y.S. Chem. Rev., 1964, 64, 353-388. [For reviews, see
[http://dx.doi.org/10.1021/cr60230a002]
(b)Rao, Y.S. Chem. Rev., 1976, 76, 625-994.
[http://dx.doi.org/10.1021/cr60303a004]
(c)Knight, D.W. Contemp. Org. Synth., 1994, 287-315.
[http://dx.doi.org/10.1039/co9940100287]
[7]
(a)Kohler, E.P.; Whitcher, W.J. J. Am. Chem. Soc., 1940, 62, 1489-1490.
[http://dx.doi.org/10.1021/ja01863a044]
(b)Asknes, G.; Froyen, P. Acta Chem. Scand., 1968, 22, 2347-2352.
[http://dx.doi.org/10.3891/acta.chem.scand.22-2347]
(c)Kresze, G.; Runge, W.; Ruth, E. Liebigs Ann. Chem., 1972, 756, 112-127.
[http://dx.doi.org/10.1002/jlac.19727560111]
(d)Musierowicz, S.; Wroblewski, A.; Krawczyk, H. Tetrahedron Lett., 1975, 437-440.
[http://dx.doi.org/10.1016/S0040-4039(00)71887-9]
(e)Kresze, G.; Kloimstein, L.; Runge, W. Liebigs Ann. Chem., 1976, 979-986.
[http://dx.doi.org/10.1002/jlac.197619760602]
(f)Gill, G.B.; Idris, M.S.H. Tetrahedron Lett., 1985, 26, 4811-4814.
[http://dx.doi.org/10.1016/S0040-4039(00)94958-X]
(g)Shingu, K.; Hagishita, S.; Nakagawa, M. Tetrahedron Lett., 1967, 4371-4374.
[http://dx.doi.org/10.1016/S0040-4039(01)89692-1]
(h)Ma, S.; Wu, S. Tetrahedron, 1999, 55, 12137-12148.
[http://dx.doi.org/10.1016/S0040-4020(99)00726-7]
(i)Ma, S.; Wu, S. Tetrahedron Lett., 2001, 42, 4075-4077.
[http://dx.doi.org/10.1016/S0040-4039(01)00634-7]
(j)Ma, S.; Pan, F.; Hao, X.; Huang, X. Synlett, 2004, 85-88.
[http://dx.doi.org/10.1055/s-2003-43377]
(k)Fu, C.; Ma, S. Eur. J. Org. Chem., 2005, 3942-3945.
[http://dx.doi.org/10.1002/ejoc.200500296]
(l)Chen, G.; Fu, C.; Ma, S. Tetrahedron, 2006, 62, 4444-4452.
[http://dx.doi.org/10.1016/j.tet.2006.02.053]
(m)Zhou, C.; Ma, Z.; Gu, Z.; Fu, C.; Ma, S. J. Org. Chem., 2008, 73, 772-774.
[http://dx.doi.org/10.1021/jo702409y]
[8]
Zimmer, R.; Dinesh, C.U.; Nadanan, E.; Hhan, F.A. Chem. Rev., 2000, 100, 3067-3125.
[http://dx.doi.org/10.1021/cr9902796]
[9]
(a)Olsson, L-I.; Claesson, A. Synthesis, 1979, 743-745.
[http://dx.doi.org/10.1055/s-1979-28825]
(b)Nikam, S.S.; Chu, K.H.; Wang, K.K. J. Org. Chem., 1986, 51, 745-747.
[http://dx.doi.org/10.1021/jo00355a034]
(c)Marshall, J.A.; Sehon, C.A. J. Org. Chem., 1995, 60, 5966-5968.
[http://dx.doi.org/10.1021/jo00123a040]
(d)Marshall, J.A.; Yu, R.H.; Perkins, J.F. J. Org. Chem., 1995, 60, 5550-5555.
[http://dx.doi.org/10.1021/jo00122a040]
[10]
(a)Chilot, J-J.; Doutheau, A.; Gore, J. Tetrahedron Lett., 1982, 23, 4693-4696.
[http://dx.doi.org/10.1016/S0040-4039(00)85689-0]
(b)Gelin, R.; Gelin, S.; Albrand, M. Bull. Soc. Chim. Fr., 1972, 1946-1949.
[11]
(a)Uemura, K.; Shiraishi, D.; Noziri, M.; Inoue, Y. Bull. Chem. Soc. Jpn., 1999, 72, 1063-1069.
[http://dx.doi.org/10.1246/bcsj.72.1063]
(b)Kang, S.K.; Baik, T.G.; Kulak, A.N. Synlett, 1999, 324-326.
[http://dx.doi.org/10.1055/s-1999-2613]
(c)Kang, S.K.; Yamaguchi, T.; Pyun, S.J.; Lee, Y.T.; Baik, T.G. Tetrahedron Lett., 1998, 39, 2127-2130.
[http://dx.doi.org/10.1016/S0040-4039(98)00076-8]
[12]
(a)Ma, S.; Gao, W. Tetrahedron Lett., 2000, 41, 8933-8936.
[http://dx.doi.org/10.1016/S0040-4039(00)01585-9]
(b)Ma, S.; Gao, W. J. Org. Chem., 2002, 67, 6104-6112.
[http://dx.doi.org/10.1021/jo0163997]
[13]
(a)Yoneda, E.; Kaneko, T.; Zhang, S-W.; Onitsuka, K.; Takahashi, S. Org. Lett., 2000, 2, 441-443.
[http://dx.doi.org/10.1021/ol990377d]
(b)Trost, B.M.; Pinkerton, A.B. J. Am. Chem. Soc., 1999, 121, 10842-10843.
[http://dx.doi.org/10.1021/ja9929537]
[14]
(a)Hoffmann-Röder, A.; Krause, N.T. Org. Biomol. Chem., 2005, 3, 387-391.
[http://dx.doi.org/10.1039/B416516K]
(b)Widenhoefer, R.A.; Han, X. Eur. J. Org. Chem., 2006, 4555-4563.
[http://dx.doi.org/10.1002/ejoc.200600399]
(c)Hashmi, A.S.K.; Hutchings, G.J. Angew. Chem. Int. Ed., 2006, 45, 7896-7936.
[http://dx.doi.org/10.1002/anie.200602454]
(d)Jimenez-Nunez, E.; Echavarren, A.M. Chem. Commun. (Camb.), 2007, 333-343.
[http://dx.doi.org/10.1039/B612008C]
(e)Gorin, D.J.; Toste, F.D. Nature, 2007, 446, 395-403.
[http://dx.doi.org/10.1038/nature05592]
(f)Bongers, N.; Krause, N. Angew. Chem. Int. Ed., 2008, 47, 2178-2181.
[http://dx.doi.org/10.1002/anie.200704729]
[15]
(a)Hoffman-Röder, A.; Krause, N. Org. Lett., 2001, 3, 2537-2538.
[http://dx.doi.org/10.1021/ol016205+]
(b)Krause, N.; Hoffman-Röder, A.; Canisius, J. Synthesis, 2002, 1759-1774.
[http://dx.doi.org/10.1055/s-2002-33707]
(c)Deutsch, C.; Gockel, B.; Hoffmann-Röder, A.; Krause, N. Synlett, 2007, 1790-1794.
[16]
(a)Brel, V.K. Synthesis, 1999, 463-466.
[http://dx.doi.org/10.1055/s-1999-3420]
(b)Brel, V.K.; Abramkin, E.V. Mendeleev Commun., 2002, 12, 64-66.
[http://dx.doi.org/10.1070/MC2002v012n02ABEH001574]
[17]
Ismailov, I.E.; Ivanov, I.K.; Christov, V.C. Bulg. Chem. Commun., Special Edition B; ; , 2017, 49, pp. 33-41.
[18]
(a)Ivanov, I.K.; Parushev, I.D.; Christov, V.C. Heteroatom Chem., 2014, 25, 60-71.
[http://dx.doi.org/10.1002/hc.21136]
(b)Ismailov, I.E.; Ivanov, I.K.; Christov, V.C. Molecules, 2014, 19, 11056-11076.
[http://dx.doi.org/10.3390/molecules190811056]
(c)Christov, V.C.; Ismailov, I.E.; Ivanov, I.K. Molecules, 2015, 20, 7263-7275.
[http://dx.doi.org/10.3390/molecules20047263]
(d)Hasanov, H.H.; Ivanov, I.K.; Christov, V.C. Phosphorus Sulfur Silicon Relat. Elem., 2018, 193, 611-619.
[http://dx.doi.org/10.1080/10426507.2018.1487432]
(e)Hasanov, H.H.; Ivanov, I.K.; Christov, V.C. Phosphorus Sulfur Silicon Relat. Elem., 2018, 193, 797-805.
[http://dx.doi.org/10.1080/10426507.2018.1515947]
(f)Hasanov, H.H.; Ivanov, I.K.; Christov, V.C. Heteroatom Chem., 2017. 28e21357
[http://dx.doi.org/10.1002/hc.21357]
[19]
(a)De la Mare, P.B.D.; Bolton, R. Electrophilic Addition to Unsaturated Systems; Elsevier: Amsterdam, The Netherlands; , 1966, pp. 250-266.
(b) Caserio, M.C. Selectivity in Addition Reactions of Allenes. Selective Organic Transformations; Thyagarajan, B.S., Ed.;John Wiley & Sons: New York, NY; , 1970, pp. 239-299.
(c)De la Mare, P.B.D.; Bolton, R. Electrophilic Addition to Unsaturated Systems; Elsevier: Amsterdam,The Netherlands; , 1982, pp. 317-325.
(d)Jacobs, T.L. Electrophilic Addition to Allenes.The Chemistry of the Allenes; Landor, S.R., Ed.;Academic Press: New York; , 1982, Vol. 2, pp. 417-510.
(e)Smadja, W. Chem. Rev., 1983, 83, 263-320.
[http://dx.doi.org/10.1021/cr00055a003]
(f)Ma, S. Ionic Addition to Allenes.Modern Allene Chemistry; Krause, N.; Hashmi, A.S.K., Eds.; Wiley-VCH: Weinheim, Germany; , 2004, Vol. 2, pp. 595-699.
[http://dx.doi.org/10.1002/9783527619573.ch10]
[20]
Baldwin, J.E. Chem. Commun., 1976, 734-736.
[http://dx.doi.org/10.1039/c39760000734]
[21]
Lecher, H.; Holschneider, F. Ber. Dtsch. Chem. Ges., 1924, 57, 755-758.
[http://dx.doi.org/10.1002/cber.19240570503]

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