A straightforward approach towards glycoamino acids and glycopeptides via Pd-catalysed allylic alkylation

Org Biomol Chem. 2009 Jan 7;7(1):103-10. doi: 10.1039/b813978d. Epub 2008 Oct 31.

Abstract

Chelated enolates are versatile nucleophiles for palladium-catalysed allylic alkylations. Even with complex allylic substrates the reaction proceed without significant isomerisation. This allows the stereoselective introduction of polyhydroxylated allylic sidechains into amino acids and peptides with retention of the olefin geometry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Catalysis
  • Chemistry / methods*
  • Drug Design
  • Glycopeptides / chemistry
  • Glycosides / chemistry*
  • Ligands
  • Models, Chemical
  • Molecular Structure
  • Palladium / chemistry*
  • Peptides / chemistry
  • Stereoisomerism
  • Threonine / chemistry

Substances

  • Amino Acids
  • Glycopeptides
  • Glycosides
  • Ligands
  • Peptides
  • Threonine
  • Palladium