Optimized synthesis of hydrogen-bond surrogate helices: Surprising effects of microwave heating on the activity of grubbs catalysts

Ross N. Chapman, Paramjit S. Arora

Research output: Contribution to journalArticle

Abstract

(Diagram presented) This manuscript discusses microwave-assisted solid-phase synthesis of hydrogen-bond surrogate based α-helices and analogues by ring-closing metathesis (RCM). Microwave-mediated RCM allows access to a greater variety of amino acid residues in the macrocycles in shorter reaction times and higher yields compared to conventional heating. Surprisingly, we discovered that the Grubbs II catalyst is highly active under the influence of microwaves but catalytically dead under oil-bath conditions for the metathesis of these peptide bisolefins.

Original languageEnglish (US)
Pages (from-to)5825-5828
Number of pages4
JournalOrganic Letters
Volume8
Issue number25
DOIs
StatePublished - Dec 7 2006

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Optimized synthesis of hydrogen-bond surrogate helices: Surprising effects of microwave heating on the activity of grubbs catalysts'. Together they form a unique fingerprint.

  • Cite this