Stereodivergency in catalytic asymmetric conjugate addition reactions of glycine (ket)imines

J Am Chem Soc. 2011 Dec 28;133(51):20750-3. doi: 10.1021/ja2100356. Epub 2011 Dec 2.

Abstract

Stereodivergent catalytic asymmetric conjugate reactions of glycine (ket)imines with nitroalkenes have been achieved using various chiral catalyst systems derived from a multidentate amino alcohol (1). The stepwise nature of the [3 + 2] cycloaddition reactions of N-metalated azomethine ylides has also been demonstrated by highly enantio- and diastereoselective syntheses of exo-5 and endo-8 from the respective syn-4 and anti-7 conjugate addition products in a one-pot tandem fashion.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Amino Alcohols / chemistry
  • Catalysis
  • Glycine / chemistry*
  • Imines / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Amino Alcohols
  • Imines
  • Glycine