A convenient and stereoselective synthesis of (Z)-allyl selenides via Sm/TMSCl system-promoted coupling of Baylis-Hillman adducts with diselenides.
- Author:
Yun-kui LIU
;
Dan-qian XU
;
Zhen-yuan XU
;
Yong-min ZHANG
- Publication Type:Journal Article
- MeSH:
Magnetic Resonance Spectroscopy;
Molecular Structure;
Organoselenium Compounds;
chemistry;
Selenium Compounds;
chemical synthesis;
chemistry;
Stereoisomerism
- From:
Journal of Zhejiang University. Science. B
2006;7(5):393-396
- CountryChina
- Language:English
-
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 S(N)2' substitution of Baylis-Hillman adducts to produce the (Z)-allyl selenides.
