Copper-catalyzed rearrangement of vinyl oxiranes

Lindsay A. Batory; Christine E. McInnis; Jon T. Njardarson

doi:10.1021/ja067073o

Copper-catalyzed rearrangement of vinyl oxiranes

Lindsay A. Batory, Christine E. McInnis, Jon T. Njardarson

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

64 Scopus citations

Abstract

A novel copper-catalyzed vinyl oxirane ring expansion protocol has been developed. A wide range of vinyl oxiranes can be rearranged to 2,5-dihydrofurans in excellent yields in the presence of electrophilic copper(II) acetylacetonate catalysts. Regioisomeric vinyl oxiranes can be converted to a single dihydrofuran product using these conditions. This method uses low catalyst loadings (0.5-5 mol %), has good tolerance of substitution patterns, and can be done in the absence of solvent.

Original language	English (US)
Pages (from-to)	16054-16055
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	128
Issue number	50
DOIs	https://doi.org/10.1021/ja067073o
State	Published - Dec 20 2006
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja067073o

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AU - Njardarson, Jon T.

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AB - A novel copper-catalyzed vinyl oxirane ring expansion protocol has been developed. A wide range of vinyl oxiranes can be rearranged to 2,5-dihydrofurans in excellent yields in the presence of electrophilic copper(II) acetylacetonate catalysts. Regioisomeric vinyl oxiranes can be converted to a single dihydrofuran product using these conditions. This method uses low catalyst loadings (0.5-5 mol %), has good tolerance of substitution patterns, and can be done in the absence of solvent.

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Copper-catalyzed rearrangement of vinyl oxiranes

Abstract

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