Asymmetric Michael Addition of <i>N</i>-<i>tert</i>-Butanesulfinyl Imidate with α,β-Unsaturated Diesters: Scope and Application to the Synthesis of Indanone Derivatives

Abstract

An additive-free and highly diastereoselective Michael addition reaction of an N-tert-butanesulfinyl imidate to α,β-unsaturated diesters has been developed using LDA as a base with good to excellent yields. The utility of this chemistry is further demonstrated by the asymmetric synthesis of 3-substituted indanone derivatives 8a, 8d, 8e, and 8i with high enantiomeric excess, which are potential building blocks for preparing biologically active lead compounds.