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

Ross N. Chapman; Paramjit S. Arora

doi:10.1021/ol062443z

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

Ross N. Chapman, Paramjit S. Arora

Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	5825-5828
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	25
DOIs	https://doi.org/10.1021/ol062443z
State	Published - Dec 7 2006

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol062443z

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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.",

author = "Chapman, {Ross N.} and Arora, {Paramjit S.}",

year = "2006",

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language = "English (US)",

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journal = "Organic Letters",

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AU - Arora, Paramjit S.

PY - 2006/12/7

Y1 - 2006/12/7

N2 - (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.

AB - (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.

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JO - Organic Letters

JF - Organic Letters

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

Abstract

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