Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Perspective

Chiral Allenylcarbonyls – Underexploited Building Blocks for Complex Synthesis

Author(s): Krishna Yadavalli* and Salvatore D. Lepore*

Volume 19, Issue 8, 2022

Published on: 01 February, 2022

Page: [597 - 601] Pages: 5

DOI: 10.2174/1570178619666211231113033

Abstract

Chiral allenylcarbonyls such as allenoates remain underutilized in complex synthesis despite recent advances in synthesis methods to prepare them non-racemically. The field is now ripe for the employment of this class of allenes as building blocks to facilitate the construction of complex small-molecule compounds, such as bridged bicycles.

Keywords: Chiral allenylcarbonyls, complex synthesis, cyclobutene, cycloaddition, zinc, diels-alder reaction.

Next »
Graphical Abstract

[1]
Wiest, J.M.; Conner, M.L.; Brown, M.K. Angew. Chem. Int. Ed. Engl., 2018, 57(17), 4647-4651.
[http://dx.doi.org/10.1002/anie.201801110] [PMID: 29481716]
[2]
Cai, L.; Zhang, K.; Kwon, O. J. Am. Chem. Soc., 2016, 138(10), 3298-3301.
[http://dx.doi.org/10.1021/jacs.6b00567] [PMID: 26910382]
[3]
Martin, C.L.; Overman, L.E.; Rohde, J.M. J. Am. Chem. Soc., 2010, 132(13), 4894-4906.
[http://dx.doi.org/10.1021/ja100178u] [PMID: 20218696]
[4]
Jung, M.E.; Cordova, J.; Murakami, M. Org. Lett., 2009, 11(17), 3882-3885.
[http://dx.doi.org/10.1021/ol901455q] [PMID: 19655733]
[5]
Jung, M.E.; Murakami, M. Org. Lett., 2007, 9(3), 461-463.
[http://dx.doi.org/10.1021/ol062811z] [PMID: 17249787]
[6]
Winkler, J.D.; Quinn, K.J.; MacKinnon, C.H.; Hiscock, S.D.; McLaughlin, E.C. Org. Lett., 2003, 5(10), 1805-1808.
[http://dx.doi.org/10.1021/ol0345226] [PMID: 12735782]
[7]
Park, S.; Pak, G.; Oh, C.; Lee, J.; Kim, J.; Yu, C-M.A. Org. Lett., 2019, 21(18), 7660-7664.
[http://dx.doi.org/10.1021/acs.orglett.9b02982] [PMID: 31486655]
[8]
Yu, S.; Ma, S. Angew. Chem. Int. Ed. Engl., 2012, 51(13), 3074-3112.
[http://dx.doi.org/10.1002/anie.201101460] [PMID: 22271630]
[9]
Kroc, M.A.; Markiewicz, M.; Pace, W.H.; Wink, D.J.; Anderson, L.L. Chem. Commun. (Camb.), 2019, 55(16), 2309-2312.
[http://dx.doi.org/10.1039/C8CC10313E] [PMID: 30720032]
[10]
Ma, S.; Yu, A.; Zhang, L.; Meng, X. J. Org. Chem., 2018, 83(10), 5410-5419.
[http://dx.doi.org/10.1021/acs.joc.8b00145] [PMID: 29688726]
[11]
Gu, Y.; Hu, P.; Ni, C.; Tong, X. J. Am. Chem. Soc., 2015, 137(19), 6400-6406.
[http://dx.doi.org/10.1021/jacs.5b03273] [PMID: 25905736]
[12]
Silvestri, M.A.; Bromfield, D.C.; Lepore, S.D. J. Org. Chem., 2005, 70(20), 8239-8241.
[http://dx.doi.org/10.1021/jo0512103] [PMID: 16277359]
[13]
Maity, P.; Lepore, S.D. J. Am. Chem. Soc., 2009, 131(12), 4196-4197.
[http://dx.doi.org/10.1021/ja810136m] [PMID: 19271702]
[14]
Bhat, B.A.; Maki, S.L.; St Germain, E.J.; Maity, P.; Lepore, S.D. J. Org. Chem., 2014, 79(19), 9402-9407.
[http://dx.doi.org/10.1021/jo501700c] [PMID: 25184784]
[15]
Neff, R.K.; Frantz, D.E. Tetrahedron, 2015, 71, 7-18.
[http://dx.doi.org/10.1016/j.tet.2014.08.030]
[16]
Han, Y.; Zhao, Y.; Ma, S. Chemistry, 2019, 25(40), 9529-9533.
[http://dx.doi.org/10.1002/chem.201900963] [PMID: 31033044]
[17]
Zhu, C.; Schwarz, J.L.; Cembellín, S.; Greßies, S.; Glorius, F. Angew. Chem. Int. Ed. Engl., 2018, 57(2), 437-441.
[http://dx.doi.org/10.1002/anie.201710835] [PMID: 29141113]
[18]
Burke, E.G.; Schomaker, J.M. Angew. Chem. Int. Ed. Engl., 2015, 54(41), 12097-12101.
[http://dx.doi.org/10.1002/anie.201504723] [PMID: 26387687]
[19]
Crouch, I.T.; Neff, R.K.; Frantz, D.E. J. Am. Chem. Soc., 2013, 135(13), 4970-4973.
[http://dx.doi.org/10.1021/ja401606e] [PMID: 23488914]
[20]
Roy, A.; Bhat, B.A.; Lepore, S.D. Org. Lett., 2016, 18(6), 1230-1233.
[http://dx.doi.org/10.1021/acs.orglett.5b03681] [PMID: 26925611]
[21]
Roy, A.; Bhat, B.A.; Lepore, S.D. Org. Lett., 2015, 17(4), 900-903.
[http://dx.doi.org/10.1021/ol503757h] [PMID: 25662282]
[22]
Roy, A.; Bhat, B.A.; Lepore, S.D. Lett. Org. Chem., 2019, 16(9), 689-696.
[http://dx.doi.org/10.2174/1570178616666181203141515] [PMID: 31316308]
[23]
Ye, J.; Ma, S. Org. Chem. Front., 2014, 1, 1210-1224.
[http://dx.doi.org/10.1039/C4QO00208C]
[24]
Lepore, S.D.; He, Y.; Damisse, P. J. Org. Chem., 2004, 69(26), 9171-9175.
[http://dx.doi.org/10.1021/jo0487754] [PMID: 15609951]
[25]
Lepore, S.D.; Khoram, A.; Bromfield, D.C.; Cohn, P.; Jairaj, V.; Silvestri, M.A. J. Org. Chem., 2005, 70(18), 7443-7446.
[http://dx.doi.org/10.1021/jo051040u] [PMID: 16122274]
[26]
Tap, A.; Blond, A.; Wakchaure, V.N.; List, B. Angew. Chem. Int. Ed. Engl., 2016, 55(31), 8962-8965.
[http://dx.doi.org/10.1002/anie.201603649] [PMID: 27275598]
[27]
Tang, Y.; Chen, Q.; Liu, X.; Wang, G.; Lin, L.; Feng, X. Angew. Chem. Int. Ed. Engl., 2015, 54(33), 9512-9516.
[http://dx.doi.org/10.1002/anie.201501918] [PMID: 26120035]
[28]
Wang, Y.; Zhang, W.; Ma, S. J. Am. Chem. Soc., 2013, 135(31), 11517-11520.
[http://dx.doi.org/10.1021/ja406135t] [PMID: 23869750]
[29]
Hashimoto, T.; Sakata, K.; Tamakuni, F.; Dutton, M.J.; Maruoka, K. Nat. Chem., 2013, 5(3), 240-244.
[http://dx.doi.org/10.1038/nchem.1567] [PMID: 23422567]
[30]
Liu, H.; Leow, D.; Huang, K-W.; Tan, C-H. J. Am. Chem. Soc., 2009, 131(21), 7212-7213.
[http://dx.doi.org/10.1021/ja901528b] [PMID: 19422238]
[31]
Grant, T.N.; West, F.G. Org. Lett., 2007, 9(19), 3789-3792.
[http://dx.doi.org/10.1021/ol7015669] [PMID: 17705503]
[32]
Song, L.; Zhu, G.; Liu, Y.; Liu, B.; Qin, S. J. Am. Chem. Soc., 2015, 137(42), 13706-13714.
[http://dx.doi.org/10.1021/jacs.5b08958] [PMID: 26434364]
[33]
Presset, M.; Coquerel, Y. Rodriguez. J. Chem. Rev., 2013, 113(1), 525-595.
[http://dx.doi.org/10.1021/cr200364p] [PMID: 23082820]
[34]
Lefranc, A.; Gremaud, L.; Alexakis, A. Org. Lett., 2014, 16(20), 5242-5245.
[http://dx.doi.org/10.1021/ol502171h] [PMID: 25275702]
[35]
Ren, Y.; Presset, M.; Godemert, J.; Vanthuyne, N.; Naubron, J-V.; Giorgi, M.; Rodriguez, J.; Coquerel, Y. Chem. Commun. (Camb.), 2016, 52(39), 6565-6568.
[http://dx.doi.org/10.1039/C6CC01689H] [PMID: 27109259]
[36]
Kuramochi, A.; Usuda, H.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc., 2005, 127(41), 14200-14201.
[http://dx.doi.org/10.1021/ja055301t] [PMID: 16218611]

© 2024 Bentham Science Publishers | Privacy Policy