One‐Pot Preparation of Chiral Carbacycles from Morita–Baylis–Hillman Carbonates by an Asymmetric Allylic Alkylation/Olefin Metathesis Sequence

Abstract

AbstractAn operationally simple, one‐pot synthetic protocol for the formation of all‐carbon, highly substituted five‐ and six‐membered rings is described. In this two‐step procedure, an asymmetric allylic alkylation (AAA) of Morita–Baylis–Hillman (MBH) carbonates with allylmalononitrile, catalyzed by a chiral tertiary amine, is followed by a ring‐closing alkene metathesis (RCM) reaction. Products are obtained in high yields, and an excellent level of optical purity of some of the target compounds is achieved after just a single recrystallization.