Kinetic Resolution of Oxazinones: Rational Exploration of Chemical Space through the Design of Experiments


Renzi P., Kronig C., Carlone A., Eroksuz S. , Berkessel A., Bella M.

CHEMISTRY-A EUROPEAN JOURNAL, vol.20, no.37, pp.11768-11775, 2014 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 20 Issue: 37
  • Publication Date: 2014
  • Doi Number: 10.1002/chem.201402380
  • Title of Journal : CHEMISTRY-A EUROPEAN JOURNAL
  • Page Numbers: pp.11768-11775
  • Keywords: design of experiments, kinetic resolution, organocatalysis, squaramides, thioureas, MICHAEL ADDITION, ORGANOCATALYSTS, OPTIMIZATION, ALCOHOLS

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% (1a-g) and product ee values up to 90% (3a-g)) in a rational way by applying the Design of Experiments (DoE) approach.