Enantioselective synthesis of an all-syn four vicinal fluorine motif.
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.
Hunter
Luke
L
Centre for Biomolecular Sciences and School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, United Kingdom.
O'Hagan
David
D
Slawin
Alexandra M Z
AM
D018360:Crystallography, X-Ray; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D006845:Hydrocarbons, Fluorinated