A convenient and stereoselective synthesis of (Z)-allyl selenides via Sm/TMSCl system-promoted coupling of Baylis-Hillman adducts with diselenides.
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.
Liu
Yun-kui
YK
Xu
Dan-qian
DQ
Xu
Zhen-yuan
ZY
Zhang
Yong-min
YM
D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000737:chemistry*; D018036:Selenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D016566:Organoselenium Compounds; D018036:Selenium Compounds