Stereoselective addition of organometallic reagents to N-(tosyl) vinylsulfoximines

FW Richard, RJ Mark

Index: Jackson, Richard F. W.; Briggs, Andrew D.; Brown, Paul A.; Clegg, William; Elsegood, Mark R. J.; Frampton, Christopher Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 14 p. 1673 - 1682

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Abstract

Treatment of N-(toluene-p-sulfonyl) vinylsulfoximines 3 with methyllithium at–78° C, followed by addition of chlorotrimethylsilane, results in the efficient formation of α-silyl vinylsulfoximines 6 in good to excellent yield. Nucleophilic addition of a range of simple alkyl and aryl organometallics (lithium, copper–lithium and Grignard reagents) occurs in variable yield to give the Michael adducts 8, with organolithium reagents most effective. The ...