Combining Palladium and Chiral Organocatalysis for the Enantioselective Deconjugative Allylation of Enals via Dienamine Intermediates.

Abstract

A catalytic enantioselective deconjugative allylation of enals is reported. A variety of enals underwent this transformation in high yield and ee, and products can be readily transformed into γ-allyl enals via a Cope rearrangement without erosion of ee. This transformation was used to install the quaternary stereocenter in (S)-bakuchiol, enabling completion of a concise formal synthesis.