Enantioselective hydrogenation of N-H imines

J Am Chem Soc. 2009 Jul 29;131(29):9882-3. doi: 10.1021/ja903319r.

Abstract

N-H ketoimines 3a-3v are readily prepared in high yield via organometallic addition to nitriles and isolated as corresponding bench-stable hydrochloride salts. Homogeneous asymmetric hydrogenation of unprotected N-H ketoimines 3a-3v using Ir-(S,S)-f-binaphane as catalyst provides chiral amines 4a-4v in 90-95% yield with enantioselectivities up to 95% ee.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Hydrogenation
  • Imines / chemical synthesis*
  • Imines / chemistry
  • Stereoisomerism

Substances

  • Imines