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Journal of Zhejiang University SCIENCE B

ISSN 1673-1581(Print), 1862-1783(Online), Monthly

2006 Vol.7 No.5 P.393-396

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

ykuiliu@zjut.edu.cn; CHRC@zjut.edu.cn

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.

Key words: Stereoselective synthesis, (Z)-allyl selenides, Diselenides, Baylis-Hillman adducts, Sm/TMSCl system


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DOI:

10.1631/jzus.2006.B0393

CLC number:

O622.6

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Received:

2006-01-18

Revision Accepted:

2006-03-22

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