Diastereoselective Synthesis of 2,3,4,5,6-Pentafluoroheptanes

Daniel Farran, Alexandra M. Z. Slawin, Peer Kirsch, David O'Hagan

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

A stereocontrolled synthesis of alkanes containing five contiguous fluorine atoms is presented. The compounds were prepared by sequential fluorination of diastereoisomeric alcohol-diepoxides. The chemistry involved epoxide ring-opening with HF-NEt3 and deshydroxyfluorination reactions of free alcohols with Deoxo-Fluor, The fluorination reactions were all highly stereospecific, with all five fluorines being incorporated in three sequential steps. Three different diastereoisomers of the 2,3,4,5,6-pentafluoroheptyl motif were prepared as heptane-1,7-diol derivatives, a structural format amenable for incorporation of the vicinal pentafluoro scaffold into larger molecular architectures.

Original languageEnglish
Pages (from-to)7168-7171
Number of pages4
JournalThe Journal of Organic Chemistry
Volume74
Issue number18
DOIs
Publication statusPublished - 18 Sept 2009

Keywords

  • MEDICINAL CHEMISTRY
  • FLUORINE

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