Radical addition of nitrones to acrylates mediated by SmI2: asymmetric synthesis of gamma-amino acids employing carbohydrate-based chiral auxiliaries

Chem Commun (Camb). 2004 Sep 7:(17):1962-3. doi: 10.1039/b405141f. Epub 2004 Jul 19.

Abstract

Alkyl nitrones possessing N-substituted sugars as chiral auxiliaries were found to effectively undergo an SmI(2)-mediated radical addition to n-butyl acrylate affording gamma-amino acid derivatives with high diastereomeric control.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylates / chemistry*
  • Amino Acids / chemical synthesis*
  • Carbohydrates / chemistry*
  • Free Radicals / chemistry
  • Models, Chemical
  • Molecular Structure
  • Nitrogen Oxides / chemistry*
  • Proteins / chemistry*
  • Proteins / pharmacology
  • Stereoisomerism

Substances

  • Acrylates
  • Amino Acids
  • Carbohydrates
  • Free Radicals
  • Nitrogen Oxides
  • Proteins
  • nitrones
  • sperm motility inhibitor 2
  • n-butyl acrylate