Highly enantioselective synthesis of fluorinated gamma-amino alcohols through proline-catalyzed cross-Mannich reaction

Org Lett. 2005 Aug 4;7(16):3433-6. doi: 10.1021/ol050791f.

Abstract

A new, simple route for the synthesis of fluorinated beta-alkyl gamma-amino alcohols in optically pure form in only two steps and featuring proline catalysis from inexpensive and readily available starting materials is described. The applied strategy allows for the introduction of diversity into both the beta-fluoroalkyl and alpha-alkyl groups of these compounds. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Alcohols / chemical synthesis*
  • Amino Alcohols / chemistry
  • Catalysis
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Mannich Bases / chemistry
  • Proline / chemistry*
  • Stereoisomerism

Substances

  • Amino Alcohols
  • Hydrocarbons, Fluorinated
  • Mannich Bases
  • Proline