This work was supported by JSPS KAKENHI Grant Number 23750171 (to K.A.) and 23550116 (to K.K.), and by MEXT KAKENHI Grant number 24105506 (to K.K.).
Peptide-Catalyzed Regio- and Enantioselective Reduction of α,β,γ,δ-Unsaturated Aldehydes†
Article first published online: 5 SEP 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 44, pages 11585–11588, October 25, 2013
How to Cite
Akagawa, K., Sen, J. and Kudo, K. (2013), Peptide-Catalyzed Regio- and Enantioselective Reduction of α,β,γ,δ-Unsaturated Aldehydes. Angew. Chem. Int. Ed., 52: 11585–11588. doi: 10.1002/anie.201305004
- Issue published online: 21 OCT 2013
- Article first published online: 5 SEP 2013
- Manuscript Received: 11 JUN 2013
- JSPS. Grant Numbers: 23750171, 23550116
- MEXT. Grant Number: 24105506
- asymmetric synthesis;
- heterogeneous catalysis;
A resin-supported peptide catalyst (see box in the scheme) was used in the title reaction. The inherent regioselectivity was overcome by the peptide catalyst to promote the 1,6-selective reaction prior to 1,4-reduction. High stereoconvergence was also achieved when using a mixture of geometric isomers of the starting aldehydes. Ach=1-amino-1-cyclohexanecarboxylic acid.