A Study of Epoxyolefin Cyclizations Catalyzed by Bismuth Trifluoromethanesulfonate and Other Metal Triflates

Ram S. Mohan; Joshua R. Lacey; Peter W. Anzalone; Christopher M. Duncan; Matthew J. Hackert

A Study of Epoxyolefin Cyclizations Catalyzed by Bismuth Trifluoromethanesulfonate and Other Metal Triflates

Ram S. Mohan, Joshua R. Lacey, Peter W. Anzalone, Christopher M. Duncan, Matthew J. Hackert

Illinois Wesleyan University

Research output: Journal Article › Article › peer-review

Abstract

Epoxyolefin cyclizations have attracted considerable interest due to their importance in biosynthetic pathways. Bismuth trifluoromethanesulfonate as well as several other metal triflates are shown to be highly effective (0.1 mol %) catalysts for the cyclization of geraniolene oxide. The product composition is found to be more dependent on solvent and substrate concentration than on the nature of the metal triflate. Cyclization products are favored in CH2Cl2 and under high dilution conditions. Ether solvents favored acyclic products.

Original language	American English
Journal	Tetrahedron Letters
Volume	46
State	Published - 2005

Disciplines

Organic Chemistry

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Cite this

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title = "A Study of Epoxyolefin Cyclizations Catalyzed by Bismuth Trifluoromethanesulfonate and Other Metal Triflates",

abstract = " Epoxyolefin cyclizations have attracted considerable interest due to their importance in biosynthetic pathways. Bismuth trifluoromethanesulfonate as well as several other metal triflates are shown to be highly effective (0.1 mol %) catalysts for the cyclization of geraniolene oxide. The product composition is found to be more dependent on solvent and substrate concentration than on the nature of the metal triflate. Cyclization products are favored in CH2Cl2 and under high dilution conditions. Ether solvents favored acyclic products.",

author = "Mohan, {Ram S.} and Lacey, {Joshua R.} and Anzalone, {Peter W.} and Duncan, {Christopher M.} and Hackert, {Matthew J.}",

year = "2005",

language = "American English",

volume = "46",

journal = "Tetrahedron Letters",

}

TY - JOUR

T1 - A Study of Epoxyolefin Cyclizations Catalyzed by Bismuth Trifluoromethanesulfonate and Other Metal Triflates

AU - Mohan, Ram S.

AU - Lacey, Joshua R.

AU - Anzalone, Peter W.

AU - Duncan, Christopher M.

AU - Hackert, Matthew J.

PY - 2005

Y1 - 2005

N2 - Epoxyolefin cyclizations have attracted considerable interest due to their importance in biosynthetic pathways. Bismuth trifluoromethanesulfonate as well as several other metal triflates are shown to be highly effective (0.1 mol %) catalysts for the cyclization of geraniolene oxide. The product composition is found to be more dependent on solvent and substrate concentration than on the nature of the metal triflate. Cyclization products are favored in CH2Cl2 and under high dilution conditions. Ether solvents favored acyclic products.

AB - Epoxyolefin cyclizations have attracted considerable interest due to their importance in biosynthetic pathways. Bismuth trifluoromethanesulfonate as well as several other metal triflates are shown to be highly effective (0.1 mol %) catalysts for the cyclization of geraniolene oxide. The product composition is found to be more dependent on solvent and substrate concentration than on the nature of the metal triflate. Cyclization products are favored in CH2Cl2 and under high dilution conditions. Ether solvents favored acyclic products.

M3 - Article

VL - 46

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -