Preparation of chiral allylic alcohols using Rhizopusnigricans. Use of the Harada–Nakanishi exciton chirality method for verifying configurational assignments of allylic alcohols

Abstract

A series of (R) acyclic and cyclic allylic alcohols was prepared by enantioselective hydrolysis of acetates using Rhizopusnigricans. The configurations of the alcohols formed were established by chemical methods and, in the case of 1,2-benzocyclohepta-1,3-dien-5-yl camphanate, by X-ray crystallography. In conjunction with the Harada–Nakanishi rule, the chiroptical properties of the p-bromobenzoate esters were used to verify configurations tentatively assigned from their method of preparation.