β-fluoroamphetamines via the stereoselective synthesis of benzylic fluorides

Alexander J. Cresswell, Stephen G. Davies, James A. Lee, Paul M. Roberts, Angela J. Russell, James E. Thomson, Melloney J. Tyte

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3-OEt 2 in CH2Cl2 at -20 -°C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective SN1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted β-fluoroamphetamines.

Original languageEnglish
Pages (from-to)2936-2939
Number of pages4
JournalOrganic Letters
Volume12
Issue number13
DOIs
Publication statusPublished - 2 Jul 2010

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry

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    Cresswell, A. J., Davies, S. G., Lee, J. A., Roberts, P. M., Russell, A. J., Thomson, J. E., & Tyte, M. J. (2010). β-fluoroamphetamines via the stereoselective synthesis of benzylic fluorides. Organic Letters, 12(13), 2936-2939. https://doi.org/10.1021/ol100862s