Enantioselective Steglich Esterification for the Resolution of 1,2-Diols

Significance

Schreiner and co-workers employed their recently developed oligopeptide catalyst 3 in a kinetic resolution of trans-cycloalkane-1,2-diols 1 via an enantiodiscriminating Steglich esterification. This work builds on their previous method of employing anhydrides for the same overall transformation (Angew. Chem. Int. Ed. 2008, 47, 6180). The advantage of the current method, apart from its comparably high enantio­selectivity and scope, is the increased operational simplicity, broader availability of carboxylic acids compared to anhydrides, and in some cases, higher reaction rates and selectivities for mono­acylation.