A regio- and stereoisomeric study of allylic alcohol fluorination with a range of reagents

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Abstract

A range of dehydroxyfluorination reagents was reacted with separate diastereoisomers of a chiral allylic alcohol to explore both the regio- and stereoselectivity ratios of direct versus allylic fluorination. The allylic alcohol stereoisomers gave the same predominant fluorinated diastereoisomer indicating that the reaction proceeds with a significant S(N)1 component via an allylic carbocation intermediate, which is quenched by fluoride ion, predominantly from the least hindered face. None of the reagents displayed very high regio- or stereoselectivity, although in all cases the allylic fluorination products predominated. (c) 2009 Elsevier B.V. All rights reserved.

Original languageEnglish
Pages (from-to)537-543
Number of pages7
JournalJournal of Fluorine Chemistry
Volume130
Issue number6
DOIs
Publication statusPublished - Jun 2009

Keywords

  • Fluorination reagents
  • DAST
  • Deoxo-Fluor (TM)
  • TFEDMA
  • FLUOLEAD (TM)
  • Dehydroxyfluorination
  • MEDICINAL CHEMISTRY
  • FLUORIDES
  • ALDEHYDES
  • AGENT

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