Preparation and regioselective reactions of novel gem-difluorinated vinyloxiranes with some organometallic reagents.
Hitherto unknown, relatively labile gem-difluorinated vinyloxiranes were prepared by difluoro-Wittig reactions with alpha,beta-epoxyketones; for these vinyloxiranes alkyl groups were delivered at the fluorine-attached terminal carbon atom in an SN2' manner by RLi, while Me3Al and MeMgBr-CuCl (3: 1) introduced the Me group at the allylic epoxy carbon with retention and inversion of the original stereochemistry, respectively.
Yamazaki
Takashi
T
Graduate School of Bioscience and Bioengineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan.
Ueki
Hisanori
H
Kitazume
Tomoya
T