Kinetic Resolution of Racemic 1-Heteroarylalkanols by Asymmetric Esterification Using Diphenylacetic Acid with Pivalic Anhydride and a Chiral Acyl-transfer Catalyst

Abstract

Abstract A variety of optically active 1-heteroarylalkanols and their esters, which include heteroaromatic moieties, such as 2-furyl, 2-thienyl, 3-thienyl, 2-thiazoyl, 2-benzothiazoyl, and 2-benzoxazoyl groups, are efficiently produced by a novel asymmetric esterification. The transition states that form the desired (R)-esters from the (R)-1-heteroarylalkanols are determined by DFT calculations, and the structural features of these transition states are systematically discussed.