Highly enantioselective asymmetric hydrogenation of alpha-phthalimide ketone: an efficient entry to enantiomerically pure amino alcohols

J Am Chem Soc. 2004 Feb 18;126(6):1626-7. doi: 10.1021/ja039153n.

Abstract

A new type of alpha-phthalimide ketones was hydrogenated in excellent enantioselectivity by using a Ru-(C3-TunePhos) complex as the catalyst. Up to 10 000 turnovers have been achieved in more than 99% ee in the hydrogenation reaction. A dynamic kinetic resolution study for the synthesis of threonine was performed, and high anti selectivity (>97:3) was observed for the first time. An efficient method to synthesize enantiomerically pure amino alcohols has been developed.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amino Alcohols / chemical synthesis*
  • Catalysis
  • Hydrogenation
  • Ketones / chemistry*
  • Phthalimides / chemistry*
  • Stereoisomerism

Substances

  • Amino Alcohols
  • Ketones
  • Phthalimides