Realization of anti-SN2' selective allylation of 4-cyclopentene-1,3-diol monoester with aryl- and alkenyl-zinc reagents |
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Authors: | Nakata Kenya Kiyotsuka Yohei Kitazume Tomoya Kobayashi Yuichi |
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Institution: | Department of Biomolecular Engineering, Tokyo Institute of Technology, Box B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan. |
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Abstract: | Anti-SN2' mode of allylation of the monoester of 4-cyclopentene-1,3-diol with aryl and alkenyl anions was achieved, for the first time, with the MeOCH2CO2- group as a leaving group to which R-ZnBr and CuCl (as a catalyst) were best fitted. The aryl groups successfully installed were Ph, o- and p-MeC6H4, o-MOMOC6H4, o-MeOC6H4, and p-F-C6H4, while cis and trans alkenyl groups were attached with retention of the olefinic stereochemistries. |
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