Cooperative catalysis in highly enantioselective Mannich-type three-component reaction of a diazoacetophenone with an alcohol and an imine

Chem Commun (Camb). 2011 Jan 14;47(2):797-9. doi: 10.1039/c0cc03024d. Epub 2010 Nov 29.

Abstract

A highly enantioselective three-component reaction of a diazoacetophenone, an alcohol, and an imine catalyzed cooperatively by Rh(2)(OAc)(4) and BINOL-derived chiral phosphoric acid has been developed for the synthesis of chiral β-amino-α-hydroxyl ketones in good yield with excellent diastereo and enantio selectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetophenones / chemistry*
  • Alcohols / chemistry*
  • Azo Compounds / chemistry*
  • Catalysis
  • Imines / chemistry*
  • Mannich Bases / chemistry*
  • Naphthols / chemistry
  • Phosphoric Acids / chemistry
  • Rhodium / chemistry
  • Stereoisomerism

Substances

  • Acetophenones
  • Alcohols
  • Azo Compounds
  • BINOL, naphthol
  • Imines
  • Mannich Bases
  • Naphthols
  • Phosphoric Acids
  • Rhodium
  • phosphoric acid
  • acetophenone