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

Ross N. Chapman, Paramjit 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

Fingerprint

Microwave heating
metathesis
Microwaves
helices
Heating
Hydrogen
Hydrogen bonds
closing
hydrogen bonds
microwaves
catalysts
Catalysts
heating
synthesis
Solid-Phase Synthesis Techniques
rings
Baths
reaction time
peptides
amino acids

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Optimized synthesis of hydrogen-bond surrogate helices : Surprising effects of microwave heating on the activity of grubbs catalysts. / Chapman, Ross N.; Arora, Paramjit.

In: Organic Letters, Vol. 8, No. 25, 07.12.2006, p. 5825-5828.

Research output: Contribution to journalArticle

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