Tetrahedron

A novel synthesis, including asymmetric synthesis, of 2, 4, 4-trisubstituted 2-cyclopentenones based on the reaction of 1-chlorovinyl p-tolyl sulfoxides with acetonitrile …

D Wakasugi, T Satoh

Index: Wakasugi, Daisuke; Satoh, Tsuyoshi Tetrahedron, 2005 , vol. 61, # 5 p. 1245 - 1256

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Citation Number: 23

Abstract

Reaction of 1-chlorovinyl p-tolyl sulfoxides, which were synthesized from chloromethyl p- tolyl sulfoxide and ketones in high overall yields, with cyanomethyllithium (lithium α- carbanion of acetonitrile) gave adducts in high to quantitative yields. The adducts were treated with LDA followed by lithium α-carbanion of the homologues of acetonitrile to give 3, 5, 5-trisubstituted enaminonitriles in good to high yields. Hydrolysis of the enaminonitriles ...