Highly enantioselective one-pot, three-component Mannich-type reaction catalyzed by an N,N'-dioxide-scandium(III) complex

Chemistry. 2009 Jun 8;15(24):5884-7. doi: 10.1002/chem.200900392.

Abstract

Mild-mannered Mannich reaction: Highly enantioselective one-pot, three-component Mannich-type reaction of aldehydes, 2-aminophenol, and ketene silyl acetal with 5 mol % of a C(2)-symmetric N,N'-dioxide-based scandium(III) triflate (2:1) complex as the catalyst was achieved under mild conditions (see scheme), which facilitated the asymmetric synthesis of biologically interesting beta-amino esters.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclic N-Oxides / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Scandium
  • Stereoisomerism

Substances

  • Cyclic N-Oxides
  • Organometallic Compounds
  • Scandium