M. Nicoletti, D. O'Hagan, A. Slawin
Jan 19, 2005
Citations
0
Influential Citations
38
Citations
Journal
Journal of the American Chemical Society
Abstract
A regio- and stereoselective method for the synthesis of alpha,beta,gamma-trifluoroalkanes is described which allows the synthesis of single diastereoisomers of this structural motif. The methodology relied upon regiospecific and stereospecific hydrogen fluoride ring opening of allylic epoxides and then Sharpless cyclic sulfate methodology followed by nucleophilic fluoride attack to introduce the second fluorine. The resultant difluoro alcohol was converted to its triflate which was also displaced by fluoride ion to generate the alpha,beta,gamma-trifluoroalkanes.