Kinetic resolution of oxazinones: rational exploration of chemical space through the design of experiments

Abstract

The organocatalytic kinetic resolution of 4-substituted oxazinones has been optimised (selectivity factor S up to 98, chiral oxazinone ee values up to 99.6 % (1 a-g) and product ee values up to 90 % (3 a-g)) in a rational way by applying the Design of Experiments (DoE) approach.

Keywords: design of experiments; kinetic resolution; organocatalysis; squaramides; thioureas.