A convenient and stereoselective synthesis of (Z)-allyl selenides via Sm/TMSCl system-promoted coupling of Baylis-Hillman adducts with diselenides
Удобный и стереоселективный синтез (Z)-аллилселенидов посредством сочетания аддуктов Байлиса—Хиллмана с диселенидами в системе Sm/TMSCl
2006-04-14
SCID: 54.1/p7kxcqsv
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(Z)-allyl selenidesBaylis-Hillman adductsS(N)2' substitutionSm/TMSCl systemdiselenides
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Abstract (AI)
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.
Key Findings
1
A one-pot Sm/TMSCl-promoted coupling of diselenides with Baylis–Hillman adducts provides (Z)-allyl selenides stereoselectively.
2
The proposed mechanism involves Sm/TMSCl cleavage of diselenides to generate selenide anions.
3
The resulting selenide anions undergo S_N2′ substitution of Baylis–Hillman adducts, furnishing (Z)-allyl selenides.
4
The synthesis proceeds under mild conditions using a simple and convenient procedure.
Research Object
Baylis–Hillman adducts and diselenides undergoing Sm/TMSCl-promoted coupling
Research Subject
The stereoselective formation of (Z)-allyl selenides via diselenide cleavage and S(N)2′ substitution under mild conditions
Publication Details
Publication Date
2006-04-14
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