Synthesis and highly enantioselective hydrogenation of exocyclic enamides: (Z)-3-arylidene-4-acetyl-3,4-dihydro-2H- 1,4-benzoxazines

J Org Chem. 2005 Mar 4;70(5):1679-83. doi: 10.1021/jo048212s.

Abstract

Highly enantioselective hydrogenation of exocyclic enamides, (Z)-3-arylidene-4-acyl-3,4-dihydro-2H-benzoxazines, was achieved in up to 98.6% ee by using Rh/(R,R)-Me-Duphos complex as the catalytic system. The absolute configuration of the product was assigned as R by chemical interrelations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Catalysis
  • Hydrogenation
  • Molecular Conformation
  • Oxazines / chemical synthesis*
  • Stereoisomerism

Substances

  • Amides
  • Oxazines