Highly Diastereoselective Synthesis of Homoallylic Alcohols Bearing Adjacent Quaternary Centers Using Substituted Allylic Zinc Reagents

Abstract

Staring from readily available polysubstituted allylic chlorides, a range of polysubstituted allylic zinc chlorides were obtained using a LiCl-mediated zinc dust insertion in 55−84% yield. A highly diastereoselective synthesis of homoallylic alcohols bearing up to two adjacent quaternary centers was achieved using these polysubstituted allylic zinc reagents.