A facile stereocontrolled synthesis of anti-alpha-(trifluoromethyl)-beta-amino alcohols

Org Lett. 2000 Oct 5;2(20):3173-6. doi: 10.1021/ol000195f.

Abstract

A short stereocontrolled preparation of anti-alpha-(trifluoromethyl)-beta-amino alcohols is described, involving an initial CF(3) transfer to cinnamaldehyde and a one-step, three-component condensation of 3,3,3-trifluorolactic aldehyde, an alkenyl (aryl) boronic acid, and an amine. Applying this methodology to chiral 3,3,3-trifluorolactic aldehyde allowed us to generate an amino alcohol enantioselectively in 92% ee.

Publication types

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

MeSH terms

  • Acrolein / analogs & derivatives
  • Acrolein / chemistry
  • Aldehydes / chemical synthesis*
  • Amino Alcohols / chemical synthesis*
  • Boronic Acids / chemistry
  • Ozone / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Amino Alcohols
  • Boronic Acids
  • Ozone
  • Acrolein
  • cinnamaldehyde