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Wen Zhang, Davin Tan, Richmond Lee, Guanghu Tong, Wenchao Chen, Baojian Qi, Prof. Dr. Kuo-Wei Huang, Prof. Dr. Choon-Hong Tan and Prof. Dr. Zhiyong Jiang Highly Enantio- and Diastereoselective Reactions of γ-Substituted Butenolides Through Direct Vinylogous Conjugate Additions Angewandte Chemie International Edition 51

Article first published online: 5 SEP 2012 | DOI: 10.1002/anie.201205872

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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.

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