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Enantioselective Synthesis of an All-syn Four Vicinal Fluorine Motif

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posted on 27.12.2006, 00:00 by Luke Hunter, David O'Hagan, Alexandra M. Z. Slawin
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.