Stereoselective anti-SN2′ Mitsunobu reaction of α-hydroxy-α-alkenylsilanes |
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| Authors: | Masato HigashinoNaoko Ikeda Tetsuro ShinadaKazuhiko Sakaguchi Yasufumi Ohfune |
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| Institution: | Graduate School of Science, Department of Material Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan |
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| Abstract: | A novel silyl group-directed anti-SN2′ reaction of allylic alcohols under Mitsunobu reaction conditions is described. The Mitsunobu reaction of α-hydroxy-α-alkenylsilanes with a TBS or TIPS group gave the anti-SN2′ product, in which regio- and stereochemical outcomes of the reaction depended on the steric bulkiness of the silyl group. |
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