Synthesis of trifluoro- or difluoromethylated olefins by regio- and stereocontrolled S(N)2' reactions of gem-difluorinated vinyloxiranes |
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Authors: | Ueki Hisanori Chiba Takashi Kitazume Tomoya |
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Affiliation: | Graduate School of Bioscience and Bioengineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan. |
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Abstract: | 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. |
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