Tetraarylphosphonium salt-catalyzed formal [3+2] cycloaddition between epoxides and trichloroacetonitrile for the synthesis of β-amino alcohol derivatives

Chem Commun (Camb). 2022 Oct 20;58(84):11819-11822. doi: 10.1039/d2cc03782c.

Abstract

Efficient regioselective synthesis of β-amino alcohol derivatives, including enantioenriched ones, by a tetraarylphosphonium salt-catalyzed coupling reaction of epoxides with trichloroacetonitrile is described. Formal [3+2] cycloaddition, followed by hydrolysis, proceeded smoothly to afford N-protected β-amino alcohols in good yields.

MeSH terms

  • Amino Alcohols*
  • Catalysis
  • Cycloaddition Reaction
  • Epoxy Compounds*
  • Sodium Chloride

Substances

  • Epoxy Compounds
  • trichloroacetonitrile
  • Amino Alcohols
  • Sodium Chloride