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Peptide-Catalyzed Regio- and Enantioselective Reduction of α,β,γ,δ-Unsaturated Aldehydes

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  • 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.).

Abstract

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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.

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