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Journal of Zhejiang University SCIENCE B 2006 Vol.7 No.5 P.393~396

10.1631/jzus.2006.B0393


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


Author(s):  Liu Yun-kui, Xu Dan-qian, Xu Zhen-yuan, Zhang Yong-min

Affiliation(s):  State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, China; more

Corresponding email(s):   ykuiliu@zjut.edu.cn, CHRC@zjut.edu.cn

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


Liu Yun-kui, Xu Dan-qian, Xu Zhen-yuan, Zhang Yong-min. 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 B, 2006, 7(9): 393~396.

@article{title="A convenient and stereoselective synthesis of (Z)-allyl selenides via Sm/TMSCl system-promoted coupling of Baylis-Hillman adducts with diselenides",
author="Liu Yun-kui, Xu Dan-qian, Xu Zhen-yuan, Zhang Yong-min",
journal="Journal of Zhejiang University Science B",
volume="7",
number="5",
pages="393~396",
year="2006",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.2006.B0393"
}

%0 Journal Article
%T A convenient and stereoselective synthesis of (Z)-allyl selenides via Sm/TMSCl system-promoted coupling of Baylis-Hillman adducts with diselenides
%A Liu Yun-kui
%A Xu Dan-qian
%A Xu Zhen-yuan
%A Zhang Yong-min
%J Journal of Zhejiang University SCIENCE B
%V 7
%N 5
%P 393~396
%@ 1673-1581
%D 2006
%I Zhejiang University Press & Springer

TY - JOUR
T1 - A convenient and stereoselective synthesis of (Z)-allyl selenides via Sm/TMSCl system-promoted coupling of Baylis-Hillman adducts with diselenides
A1 - Liu Yun-kui
A1 - Xu Dan-qian
A1 - Xu Zhen-yuan
A1 - Zhang Yong-min
J0 - Journal of Zhejiang University Science B
VL - 7
IS - 5
SP - 393
EP - 396
%@ 1673-1581
Y1 - 2006
PB - Zhejiang University Press & Springer
ER -


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.

Darkslateblue:Affiliate; Royal Blue:Author; Turquoise:Article

Reference

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