Synthesis and separation of two stereoisomers of deuterated tetrasubstituted allylic alcohols via consecutive dual 1,2-metallate shifts

Abstract

Herein, we report an efficient strategy for the synthesis and stereoisomer separation of deuterated tetrasubstituted allylic alcohols from alkynyl tetracoordinate boron species using readily available D₂O as the deuterium source in a single vessel system. This transformation proceeds via consecutive dual 1,2-metallate shifts, achieving efficient construction of both isomeric deuterated allylic alcohols without the requirement for condition optimization or the selection of special reagents and substrates upon oxidation. And the method features quantitative deuterium incorporation (>99%), broad substrate scope, and direct access to pharmaceutically relevant scaffolds under mild conditions.