One-pot kinetic resolution–Mitsunobu reaction to access optically pure compounds, using silver salts in the substitution protocol

Abstract

A practical method is developed to access chiral arylalkyl carbinols with a high yield from racemic alcohols. A one-pot enzyme mediated Kinetic Resolution followed by Mitsunobu esterification of the unreacted enantiomer of alcohol with metal acetate results in a nearly complete formation of chiral acetate. Substitution with AgOAc was found to be the most efficient, and the use of sub stoichiometric amounts of AgNO₃ and excess of NaOAc affords comparable results; the protocol was further extended to introduce azide as a nucleophile.