Preparation of α-amino acids by oxidative oxazoline-oxazinone rearrangement-hydrogenation (OOOH). Scope and limitations

Chem Asian J. 2011 Aug 1;6(8):2022-7. doi: 10.1002/asia.201100452. Epub 2011 Jul 12.

Abstract

The range and scope of the oxidative oxazoline-oxazinone rearrangement-hydrogenation sequence (OOOH)--a short, direct asymmetric synthesis of α-amino acids from carboxylic acids--was explored. The highest yet reported diastereoselectivity for hydrogenation of the oxazinone C=N bond (d.r.=>80:1) is disclosed and rationalized with the aid of ab initio molecular calculations.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Carboxylic Acids / chemistry
  • Catalysis
  • Hydrogenation
  • Models, Molecular
  • Oxazines / chemistry*
  • Oxazoles / chemistry*
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Amino Acids
  • Carboxylic Acids
  • Oxazines
  • Oxazoles