Stereochemistry of nucleophilic addition reactions. 6. Synthesis of isoxazoline N-oxide derivatives from methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-.ALPHA.-D-erythro-hex-2-enopyranoside with some S-ylides.
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概要
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In the reactions of dimethyloxosulfonium methylide, dimethylsulfonium ethoxycarbonylmethylide, and dimethylsulfonium phenacylide with the title compound, axial attack predominates over equatorial attack, particularly in the case of dimethylsulfonium phenacylide equatorial attack being no longer observed. Axial attack afforded exclusively 1,4-addition products (isoxazoline <I>N</I>-oxide derivatives), whereas equatorial attack gave only 1,2-addition products (cyclopropane and stabilized ylide, respectively). Discussion is given on such high selectivities.
- 公益社団法人 日本化学会の論文
著者
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Sakakibara Tohru
Department Of Chemistry Yokohama City University
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Sudoh Rokuro
Department of Chemistry, Faculty of Science, Tokyo Institute of Technology
関連論文
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