Nucleophilic Conjugate 1,5-Addition of Gilman Reagents to (E)-Hex-2-en-4-ynedioates: An Access to ()-Substituted Muconates

Abstract

An unusual nucleophilic conjugate addition of organocuprates to enynedioates resulted in chemo- and regioselective formation of ()-addition products, rather than ()-addition products, in moderate to good yields. This addition pattern is different from that with organophosphanes or alkyl amines, and presents a short and efficient method for the preparation of various ()-alkyl- or -aryl-substituted muconates compared with other synthetic approaches.