Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles

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Abstract

The Prins reaction was investigated using BF3 center dot OEt2 as a Lewis acid. It has been recently demonstrated, that if BF3 center dot OEt2 is used in stoichiometric amounts then these reactions generate fluorinated products where the BF3 center dot OEt2 contributes fluoride ion to quench the intermediate carbocations. In this study oxa- and aza-Prins reactions for the synthesis of 4-fluoro-pyrans and -piperidines were investigated. The products were obtained in good yields, but only with moderate diastereoselectivity. These Prins fluorination reactions can be accelerated under microwave conditions. The study extends the Prins fluorination methodology for the generation of the C-F bond in heterocycles.

Original languageEnglish
Article number41
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume6
DOIs
Publication statusPublished - 26 Apr 2010

Keywords

  • 4-fluoropiperidine
  • 4-fluoropyran
  • Heterocycles
  • Organo-fluorine
  • Chemistry
  • Prins cyclisation
  • Expeditious synthesis
  • Tetrahydropyrans
  • Exchange
  • Facile
  • Esters
  • Cope

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