Enantioselective synthesis of an all-syn four vicinal fluorine motif |
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Authors: | Hunter Luke O'Hagan David Slawin Alexandra M Z |
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Affiliation: | Centre for Biomolecular Sciences and School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, United Kingdom. |
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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. |
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