General synthesis of C-glycosyl amino acids via proline-catalyzed direct electrophilic alpha-amination of C-glycosylalkyl aldehydes

Org Lett. 2008 Oct 16;10(20):4485-8. doi: 10.1021/ol801685x. Epub 2008 Sep 13.

Abstract

Non-natural axially and equatorially linked C-glycosyl alpha-amino acids (glycines, alanines, and CH2-serine isosteres) with either S or R alpha-configuration were prepared by D- and L-proline-catalyzed (de >95%) alpha-amination of C-glycosylalkyl aldehydes using dibenzyl azodicarboxylate as the electrophilic reagent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis*
  • Aldehydes / chemistry
  • Alkylation
  • Amination
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Catalysis
  • Electrons*
  • Glycosylation
  • Molecular Structure

Substances

  • Aldehydes
  • Amino Acids