Enantioselective synthesis of an all-syn four vicinal fluorine motif

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Abstract

Alkanes bearing multiple vicinal fluorine atoms at adjacent stereocenters may be considered intermediate between alkanes and perfluoroalkanes, and as a class, their chemistry and behavior remain to be explored. We report here a stereoselective synthesis of an all-syn four vicinal fluorine motif as a single enantiomer. The four vicinal fluorine compound was amenable to single-crystal X-ray analysis, and the resulting structure displays gauche relationships between all four fluorines, consistent with the fluorine gauche effect, and CF···HC hydrogen bonding between adjacent fluoroalkyl chains.
Original languageEnglish
Pages (from-to)16422-16423
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number51
DOIs
Publication statusPublished - 27 Dec 2006

Keywords

  • BIS(2-METHOXYETHYL)AMINOSULFUR TRIFLUORIDE
  • STABILITY
  • EPOXIDES
  • FLUORINE
  • REAGENT

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