Ring-opening hydrofluorination of 2,3- and 3,4-epoxy amines by HBF 4·OEt2: Application to the asymmetric synthesis of (S, S)-3-deoxy-3-fluorosafingol

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

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Treatment of a range of 2,3- and 3,4-epoxy amines with HBF 4·OEt2 at room temperature results in fast and efficient SN2-type ring-opening hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method. The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.

Original languageEnglish
Pages (from-to)4617-4627
Number of pages11
JournalJournal of Organic Chemistry
Volume76
Issue number11
DOIs
Publication statusPublished - 3 Jun 2011

ASJC Scopus subject areas

  • Organic Chemistry

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