Kinetic Resolution of 5-Substituted Oxazinones with Bifunctional Chiral Base/Squaramide Organocatalysts

Eroeksuez S. , Neudoerfl J. M. , Berkessel A.

SYNLETT, vol.28, no.11, pp.1278-1281, 2017 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 28 Issue: 11
  • Publication Date: 2017
  • Doi Number: 10.1055/s-0036-1588852
  • Title of Journal : SYNLETT
  • Page Numbers: pp.1278-1281


5-Substituted oxazinones provide N-protected beta(2)-amino acid esters upon alcoholytic ring opening. Thus far, this access to enantiopure beta(2)-amino acids has been restricted to the use of enzymes (hydrolases) as catalysts for the kinetic resolution of racemic 5-substituted oxazinones, and branched alkyl or ortho-substituted aryl groups on the substrate oxazinone's 5-position were typically not tolerated. We herein report that certain bifunctional chiral base/squaramide organocatalysts, in particular those derived from cis-1,2-diaminocyclohexane or 9-amino-9-epi-quinine, allow the first organocatalytic kinetic resolution of this 'difficult' class of oxazinone substrates, affording N-protected beta(2)-amino acid esters with selectivity factors up to 43.