A facile and efficient method for the rearrangement of aryl-substituted epoxides to aldehydes and ketones using bismuth triflate

Kaushik A. Bhatia, Kyle J. Eash, Nicholas M. Leonard, Matthew C. Oswald, Ram S. Mohan

Research output: Contribution to journalArticlepeer-review

104 Scopus citations

Abstract

Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01-0.1 mol% Bi(OTf)3·xH2O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C-O bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF3·Et2O, currently used to effect epoxide rearrangements.

Original languageEnglish (US)
Pages (from-to)8129-8132
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number46
DOIs
StatePublished - Nov 12 2001

Keywords

  • Bismuth and compounds
  • Epoxides
  • Rearrangements

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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