General, Mild, and Metal-Free Synthesis of Phenyl Selenoesters from Anhydrides and Their Use in Peptide Synthesis

J Org Chem. 2017 May 5;82(9):4588-4603. doi: 10.1021/acs.joc.7b00173. Epub 2017 Apr 25.

Abstract

A mild, practical, and simple procedure for phenyl selenoesters synthesis from several anhydrides and diphenyl diselenide was developed. This transition-metal-free method provides a straightforward entry to storable Fmoc-amino acid selenoesters which are effective chemoselective acylating reagents. An application to oligopeptide synthesis was illustrated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Anhydrides / chemistry*
  • Esters / chemistry
  • Metals / chemistry*
  • Peptides / chemical synthesis*
  • Selenium / chemistry*

Substances

  • Anhydrides
  • Esters
  • Metals
  • Peptides
  • Selenium