A method for cleaving an allyl protecting group at the amide nitrogen of peptides by one-pot olefin isomerization-oxidation

J Org Chem. 2008 Dec 5;73(23):9494-6. doi: 10.1021/jo801915c.

Abstract

A facile method for N-deallylation at the amide nitrogen of peptides is described. One-pot deallylation of a substrate through ruthenium hydride-catalyzed terminal olefin isomerization and subsequent ozonolysis gave the corresponding deallylated product under mild conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Amides / chemistry*
  • Chemistry, Organic / methods*
  • Drug Design
  • Models, Chemical
  • Nitrogen / chemistry*
  • Oxygen / chemistry*
  • Ozone
  • Peptides / chemistry*
  • Ruthenium / chemistry

Substances

  • Alkenes
  • Amides
  • Peptides
  • Ozone
  • Ruthenium
  • Nitrogen
  • Oxygen