Chemo-Enzymatic Enantioconvergent Synthesis of C₄-Building Blocks Containing a Fully Substituted Chiral Carbon Center using Bacterial Epoxide Hydrolases

Abstract

A highly efficient chemo-enzymatic asymmetric synthesis of chiral C4-building blocks containing a fully substituted carbon center is reported. The key transformation consists of a deracemization based on an enantioconvergent asymmetric hydrolysis of an epoxide using combined bio- and chemo-catalysis leading to a single enantiomeric product in >98% e. e. A simple switch of steps leads to kinetic resolution giving access to products of opposite configuration.