These authors contributed equally to this work.
Highly Enantio- and Diastereoselective Reactions of γ-Substituted Butenolides Through Direct Vinylogous Conjugate Additions†
Article first published online: 5 SEP 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 40, pages 10069–10073, October 1, 2012
How to Cite
Zhang, W., Tan, D., Lee, R., Tong, G., Chen, W., Qi, B., Huang, K.-W., Tan, C.-H. and Jiang, Z. (2012), Highly Enantio- and Diastereoselective Reactions of γ-Substituted Butenolides Through Direct Vinylogous Conjugate Additions . Angew. Chem. Int. Ed., 51: 10069–10073. doi: 10.1002/anie.201205872
This work was supported by the NSFC (21072044) and the Excellent Youth Foundation of Henan Scientific Committee (114100510003) to Z.J., and by KAUST to K.-W. H.
- Issue published online: 26 SEP 2012
- Article first published online: 5 SEP 2012
- Manuscript Received: 24 JUL 2012
- NSFC. Grant Number: 21072044
- Excellent Youth Foundation of Henan Scientific Committee. Grant Number: 114100510003
- asymmetric catalysis;
- Michael addition;
- vinylogous conjugate addition
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.