Multicomponent Reaction of Aliphatic Organozinc Reagents, Acrylates and Acyl chlorides: Synthesis of α‐Substituted β‐Ketoesters

Abstract

An uncatalyzed three‐component reaction employing aliphatic organozinc reagents for the preparation of α‐substituted β‐ketoesters is described. This modular procedure, which relies on a formal conjugate addition/crossed‐Claisen domino reaction between an organozinc, an acrylate and an acyl chloride, allows the straightforward synthesis of the reaction products under mild conditions. The three‐component coupling can also be conducted from alkyl iodides, in an even more simple procedure. Experimental findings account for a probable polar concerted mechanism involving at least two organozinc compounds at the stage of the transition state.