Kinetic resolution of racemic tertiary allylic alcohols through SN2' reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system

Chem Sci. 2022 Jul 20;13(33):9607-9613. doi: 10.1039/d2sc03052g. eCollection 2022 Aug 24.

Abstract

A highly efficient kinetic resolution (KR) of racemic tertiary allylic alcohols was achieved through an intramolecular allylic substitution reaction using a co-catalyst system composed of chiral bisphosphoric acid and silver carbonate. This reaction afforded enantioenriched diene monoepoxides along with the recovery of tertiary allylic alcohols in a highly enantioselective manner, realizing an extremely high s-factor in most cases. The present method provides a new access to enantioenriched tertiary allylic alcohols, multifunctional compounds that are applicable for further synthetic manipulations.