Please use this identifier to cite or link to this item: https://doi.org/10.1021/ja901528b
Title: Enantioselective synthesis of chiral allenoates by guanidine-catalyzed isomerization of 3-alkynoates
Authors: Liu, H.
Leow, D.
Huang, K.-W. 
Tan, C.-H. 
Issue Date: 3-Jun-2009
Citation: Liu, H., Leow, D., Huang, K.-W., Tan, C.-H. (2009-06-03). Enantioselective synthesis of chiral allenoates by guanidine-catalyzed isomerization of 3-alkynoates. Journal of the American Chemical Society 131 (21) : 7212-7213. ScholarBank@NUS Repository. https://doi.org/10.1021/ja901528b
Abstract: (Chemical Equation Presented) We report that chiral bicyclic guanidine 1 is found to catalyze the isomerization of alkynes to chiral allenes with high enantioselectivities. This Brønsted base catalyzed 1,3-proton shift reaction, an efficient and atom economical reaction, proceeds through deprotonation and protonation sequences. The axial chirality of the allenes is efficiently transferred to functionalized butenolides and cycloaddition products. We also successfully demonstrate the stereospecific synthesis of butenolide through allenoate cyclization with a catalytic cationic Au(I) complex. Copyright © 2009 American Chemical Society.
Source Title: Journal of the American Chemical Society
URI: http://scholarbank.nus.edu.sg/handle/10635/76108
ISSN: 00027863
DOI: 10.1021/ja901528b
Appears in Collections:Staff Publications

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