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

Research output: Journal ArticleArticlepeer-review


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 languageAmerican English
JournalTetrahedron Letters
StatePublished - 2005


  • Organic Chemistry

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