The Catalytic Asymmetric α-Benzylation of Aldehydes

List B., Čoric̈ I., Grygorenko O., Kaib P., Komarov I., Lee A., Leutzsch M., Chandra Pan S., Tymtsunik A., van Gemmeren M.

Abstract

The first aminocatalyzed α-alkylation of α-branched aldehydes with benzyl bromides as alkylating agents has been developed. Using a sterically demanding proline derived catalyst, racemic α-branched aldehydes are reacted with alkylating agents in a DYKAT process to give the corresponding α-alkylated aldehydes with quaternary stereogenic centers in good yields and high enantioselectivities. A sterically demanding proline derivative promotes the first aminocatalyzed α-alkylation of α-branched aldehydes with benzyl bromides as alkylating agents. Racemic α-branched aldehydes react with alkylating agents in a DYKAT process to give the corresponding α-alkylated aldehydes with quaternary stereogenic centers in good yields and high enantioselectivities. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.