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The effect of fluoromethyl groups on the diastereoselectivity in the electrophilic alkylation
Authors:Kenji Tamura  Tomoya Kitazume  Toshio Kubota
Affiliation:a Graduate School of Bioscience and Bioengineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan
b Department of Applied Chemistry, Tokyo University of Agriculture and Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
c Department of Materials Science, Ibaraki University, 4-12-1 Nakanarusawa, Hitachi, Ibariki 316-8511, Japan
Abstract:The effect of fluoromethyl groups on the diastereoselectivity in the electrophilic alkylation is described. In particular, the electrophilic alkylation of enolates with a trifluoromethyl group was proceeded with highly diastereofacial selectivity based on the steric and/or electrostatic effect of substituent with strong electron withdrawing.
Keywords:Diastereoselectivity   Electrophilic alkylation
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