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A convenient and stereoselective synthesis of (Z)-allyl selenides via Sm/TMSCl system-promoted coupling of Baylis-Hillman adducts with diselenides

A convenient and stereoselective synthesis of (Z)-allyl selenides via Sm/TMSCl system-promoted coupling of Baylis-Hillman adducts with diselenides
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摘要 A simple and convenient procedure for stercoselective synthesis of (Z)-allyl selenides has been developed by a one-pot reaction of diselenides with Baylis-Hillman adducts in the presence of samarium metal-trimethylsilyl chloride under mild conditions. Presumably, the diselenides are cleaved by Sm/TMSCI system to form selemde anions, which then undergo SN2' substitution of Baylis-Hillman adducts to produce the (Z)-allyl selenides. A simple and convenient procedure for stereoselective synthesis of (Z)-allyl selenides has been developed by a one-pot reaction of diselenides with Baylis-Hillman adducts in the presence of samarium metal-trimethylsilyl chloride under mild condi-tions. Presumably, the diselenides are cleaved by Sm/TMSCl system to form selenide anions, which then undergo SN2′ substitution of Baylis-Hillman adducts to produce the (Z)-allyl selenides.
出处 《Journal of Zhejiang University-Science B(Biomedicine & Biotechnology)》 SCIE CAS CSCD 2006年第5期393-396,共4页 浙江大学学报(英文版)B辑(生物医学与生物技术)
基金 Project (No. 2004C21032) supported by the Key Technologies R &D Program of Zhejiang Province, China
关键词 Stereoselective synthesis (Z)-allyl selenides DISELENIDES Baylis-Hillman adducts Sm/TMSCI system 立体选择性分析 烯丙基硒化物 联硒化物 Baylis-Hillman络合物 TMSCI
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