Synthesis of trifluoro- or difluoromethylated olefins by regio- and stereocontrolled S(N)2' reactions of gem-difluorinated vinyloxiranes.
This paper presents a highly stereoselective synthesis of trifluoro- or difluoromethylated olefins via an S(N)2' type fluorination or reductions of gem-difluorinated vinyloxiranes. Their fluorination with HF-Py furnished trifluoromethylated allylic alcohols with exclusive E selectivity. On the other hand, their reduction with DIBAL-H afforded difluoromethylated E-allylic alcohols predominantly, whereas the corresponding Z isomers were formed exclusively by treatment with BH3.THF.
Ueki
Hisanori
H
Graduate School of Bioscience and Bioengineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan.
Chiba
Takashi
T
Kitazume
Tomoya
T
D000475:Alkenes / Q000138:chemical synthesis*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000475:Alkenes; D006845:Hydrocarbons, Fluorinated