A novel synthesis of 2, 4, 4-trisubstituted 2-cyclopentenones by consecutive reaction of 1-chlorovinyl p-tolyl sulfoxides with acetonitrile and its homologues

T Satoh, D Wakasugi

Index: Satoh, Tsuyoshi; Wakasugi, Daisuke Tetrahedron Letters, 2003 , vol. 44, # 40 p. 7517 - 7520

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Citation Number: 16

Abstract

1-Chlorovinyl p-tolyl sulfoxides were synthesized from several kinds of ketones and chloromethyl p-tolyl sulfoxide in three steps in high overall yields. Treatment of the 1- chlorovinyl p-tolyl sulfoxides with cyanomethyllithium (lithium α-carbanion of acetonitrile) at low temperature gave the adducts in almost quantitative yields. The adducts were then treated with LDA followed by excess lithium α-carbanion of the homologues of acetonitrile ...