Enantioselective radical addition/trapping reactions with alpha,beta-disubstituted unsaturated imides. Synthesis of anti-propionate aldols

J Am Chem Soc. 2005 Mar 2;127(8):2390-1. doi: 10.1021/ja043371e.

Abstract

This manuscript describes a highly diastereo- and enantioselective intermolecular radical addition/hydrogen atom transfer to alpha,beta-disubstituted enoates. Additionally, we show that anti-propionate aldol-like products can be easily prepared from alpha-methyl-beta-acyloxyenoates in good yields and high diastereo- and enantioselectivities.

Publication types

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

MeSH terms

  • Aldehydes / chemical synthesis*
  • Aldehydes / chemistry
  • Free Radicals / chemistry
  • Imides / chemistry*
  • Propionates / chemical synthesis*
  • Propionates / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Free Radicals
  • Imides
  • Propionates