Highly enantioselective synthesis of chiral cyclic amino alcohols and conhydrine by ruthenium-catalyzed asymmetric hydrogenation

Org Lett. 2009 Nov 5;11(21):4994-7. doi: 10.1021/ol901605a.

Abstract

A highly efficient enantio- and diastereoselective synthesis of chiral cis-beta-N-alkyl/arylamino cyclic alcohols has been realized by asymmetric hydrogenation of racemic alpha-amino cyclic ketones via DKR catalyzed by [RuCl(2)((S)-Xyl-SDP)((R,R)-DPEN)]. The enantioselectivities of the reaction were up to 99.9% ee with 99:1 cis-selectivities. A practical catalytic asymmetric synthesis of all four isomers of conhydrine was also developed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Amino Alcohols / chemical synthesis*
  • Amino Alcohols / chemistry
  • Catalysis
  • Hemlock / chemistry
  • Hydrogenation
  • Molecular Structure
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Ruthenium / chemistry*
  • Stereoisomerism

Substances

  • Alkaloids
  • Amino Alcohols
  • Piperidines
  • alpha-conhydrine
  • Ruthenium