Asymmetric synthesis of chiral aldehydes by conjugate additions with bifunctional organocatalysis by cinchona alkaloids

Abstract

A highly efficient asymmetric conjugate addition of carbonyl donors to α,β-unsaturated aldehydes is realized with 6′-OH cinchona alkaloids as bifunctional organocatalysts. A wide range of α-substituted β-ketoesters and α-substituted α-cyanoacetates can be employed as donors, whereas acrolein and β-substituted α,β-unsaturated aldehydes are suitable acceptors for this enantioselective addition. (Chemical Equation Presented) © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.