ChemInform Abstract: A Peterson Olefination Reaction Using Silyl-Substituted Sulfonamide Carbanions. Synthesis of Vinylic Sulfonamides.

Abstract

Abstract α-Trimethylsilyl-substituted sulfonamides RCH(SiMe3)SO2N(CH3)2 (3), (R[dbnd]H, CH3 and C6H5) are synthetized 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[dbnd]H, the reaction is highly E-stereoselective. Moderate stereoselectivity is obtained in the cases of R[dbnd]CH3 and R[dbnd]C6H5.