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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 |
| Liu Yun-kui, Xu Dan-qian, Xu Zhen-yuan, Zhang Yong-min |
| State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, China; 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.
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Received: 18 January 2006
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