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Highly regio- and stereocontrolled SN2′ reactions of gem-difluorinated vinyloxiranes with monoalkylcopper reagents |
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| Authors: | Hisanori Ueki Takashi Yamazaki Tomoya Kitazume |
| Institution: | a Graduate School of Bioscience and Bioengineering, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8501, Japan b Center of Future Nano-materials, Institute of Symbiotic Sciences and Technology, Tokyo University of Agriculture and Technology, 2-24-16, Nakamachi, Koganei 184-8588, Japan |
| Abstract: | Reaction of gem-difluorinated vinyloxiranes with RCu(X)Li allowed us to introduce the R group regioselectively at the fluorine-attached terminal carbon atom in an SN2′ manner to afford (E)-allylic alcohols exclusively, while homoallylic alcohols with anti stereochemical relationship were found to be obtained selectively from higher-ordered cuprates derived from CuCl and RMgBr in a ratio of 1:3. |
| Keywords: | Cuprate SN2&prime reaction SN2 reaction Inversion AlR3 Retention |
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