A general organocatalytic enantioselective malonate addition to α,β-unsaturated enones

Abstract

A general enantioselective organocatalytic conjugate addition procedure of a variety of malonates to α,β-unsaturated enone systems is presented. The reaction is efficiently catalysed by the pyrrolidinyl tetrazole catalyst 1. Cyclic, acyclic and aromatic enones can be used and the reaction with ethyl malonates 3b provides the Michael addition products in high yields with good to excellent enantioselectivities. Since only 1.5 equivalents of malonate are used as a reagent, the reaction is readily scaled and practical to operate. Furthermore, the malonate addition products can be easily mono decarboxylated without loss in enantiomeric excess by enzymatic or sodium hydroxide mediated methods. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.