| A convenient and stereoselective synthesis of （Z）-allyl selenides via Sm/TMSCI system-promoted coupling of Baylis-Hillman adducts with diselenides |
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| 作者姓名： | Liu YK Xu DQ Xu ZY Zhang YM |
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| 作者单位： | [1]State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, China [2]Department of Chemistry, Zhejiang University. Hang＇zhou 310028, China |
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| 基金项目： | Project （No. 2004C21032） supported by the Key Technologies R ＆ D Program of Zhejiang Province, China |
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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.
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| 关 键 词： | 立体选择性分析 烯丙基硒化物 联硒化物 Baylis-Hillman络合物 钐 TMSCI |
| 收稿时间： | 2006-01-18 |
| 修稿时间： | 2006-03-22 |
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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| Liu YK,Xu DQ,Xu ZY,Zhang YM.A convenient and stereoselective synthesis of (Z)-allyl selenides via Sm/TMSCl system-promoted coupling of Baylis-Hillman adducts with diselenides[J].Journal of Zhejiang University Science,2006,7(5):393-396. |
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| Authors: | Yun-kui Liu Dan-qian Xu Zhen-yuan Xu Yong-min Zhang |
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| Institution: | (1) State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou, 310014, China;(2) Department of Chemistry, Zhejiang University, Hangzhou, 310028, China |
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| Abstract: | 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 conditions. 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.
Project (No. 2004C21032) supported by the Key Technologies R & D Program of Zhejiang Province, China |
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| Keywords: | Stereoselective synthesis (Z)-allyl selenides Diselenides Baylis-Hillman adducts Sm/TMSCl system |
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