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Wiley, Angewandte Chemie International Edition, 40(51), p. 10069-10073, 2012

DOI: 10.1002/anie.201205872

Wiley, Angewandte Chemie, 40(124), p. 10216-10220, 2012

DOI: 10.1002/ange.201205872

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Highly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions

Journal article published in 2012 by Wen Zhang, Davin Tan, Richmond Lee, Guanghu Tong, Wenchao Chen, Baojian Qi, Kuo-Wei Huang ORCID, Choonhong Tan, Zhiyong Jiang
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

The strength of the weak: An L-tert-leucine-derived amine-thiourea catalyst (see scheme, green box) promotes the asymmetric vinylogous conjugate addition reaction between γ-aryl- and alkyl-substituted butenolides with the butenamides and enoates shown. Computational studies show the preference for the observed stereochemistry is a result of favourable weak non-bonding interactions, which stabilize the transition state. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.