2891-97-6Relevant academic research and scientific papers
A PETERSON OLEFINATION REACTION USING SILYL-SUBSTITUTED SULFONAMIDE CARBANIONS. SYNTHESIS OF VINYLIC SULFONAMIDES
Mladenova, Margarita,Gaudemar-Bardone, Francoise
, p. 257 - 268 (2007/10/02)
α-Trimethylsilyl-substituted sulfonamides RCH(SiMe3)SO2N(CH3)2 (3), (R=H, CH3 and C6H5) are synthesized in almost quantitative yields.Their lithium derivatives 4 undergo a smooth Peterson olefination reaction with nonenolisable carbonyl compounds to give good to excellent yields of vinylsulfonamides 6.With R=H, the reaction is highly E-stereoselective.Moderate stereoselectivity is obtained in the cases of R=CH3, and R=C6H5.Key words: Peterson olefination reaction; N,N-dimethyl α-trimethylsilylsulfonamides; α-trimethylsilyl-substituted sulfonamide carbanions; vinylic sulfonamides; stereochemistry.
