Use of bis-(chiral alpha-methylbenzyl)glycine esters for synthesis of enantiopure beta-hydroxyamino esters

Org Lett. 2003 Sep 4;5(18):3305-8. doi: 10.1021/ol030085j.

Abstract

[reaction: see text] Aldol reactions using bis-(chiral alpha-methylbenzyl)glycine esters with aldehydes gave excellent diastereoselectivity. Thus, an enantiopure ribosylglycine was prepared for the synthesis of analogues of the natural antibiotics muraymycin. This method was extended for formation of beta-hydroxyamino esters.

MeSH terms

  • Aldehydes / chemistry
  • Anti-Bacterial Agents / chemical synthesis
  • Crystallography, X-Ray
  • Esters / chemical synthesis*
  • Glycine / analogs & derivatives*
  • Hydroxamic Acids / chemical synthesis*
  • Molecular Structure
  • Nucleotides
  • Peptides
  • Peptidoglycan / analogs & derivatives*
  • Peptidoglycan / chemistry
  • Stereoisomerism
  • Urea

Substances

  • Aldehydes
  • Anti-Bacterial Agents
  • Esters
  • Hydroxamic Acids
  • Nucleotides
  • Peptides
  • Peptidoglycan
  • muraymycin A1
  • Urea
  • Glycine