A Chiral Pentafluorinated Isopropyl Group via Iodine(I)/(III) Catalysis
An I(I)/(III) catalysis strategy to construct an enantioenriched fluorinated isostere of the iPr group is reported. The difluorination of readily accessible α-CF3-styrenes is enabled by the in situ generation of a chiral ArIF2 species to forge a stereocentre with the substituents F, CH2F and CF3 (up to 95 %, >20:1 vicinal:geminal difluorination). The replacement of the metabolically labile benzylic proton results in a highly preorganised scaffold as was determined by X-ray crystallography (π→σ* and stereoelectronic gauche σ→σ* interactions). A process of catalyst editing is disclosed in which preliminary validation of enantioselectivity is placed on a structural foundation.
Meyer, Stephanie,H?fliger, Joel,Sch?fer, Michael,Molloy, John J.,Daniliuc, Constantin G.,Gilmour, Ryan
A successful perfluoroalkylation of various carbanions by the use of perfluoroalkylphenyliodonium trifluoromethanesulfonate (FITS) was described.The reactivity of other perfluoroalkyliodonium salt was also examined.
Umemoto, Teruo,Kuriu, Yuriko
p. 5197 - 5200
(2007/10/02)
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