Tetrahedron

A general preparative method for carbonyl-protected γ-lithioketones via reductive lithiation. Synthetic uses of the bishomoenolate equivalents

T Cohen, B Zhang, JP Cherkauskas

Index: Cohen, Theodore; Zhang, Birong; Cherkauskas, John P. Tetrahedron, 1994 , vol. 50, # 40 p. 11569 - 11584

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Citation Number: 25

Abstract

The mixed cuprates, generated by reductive lithiation of bis (phenylthio) acetals using lithium 4, 4′-di-tert-butylbiphenylide (LDBB), followed by addition of cuprous bromide- dimethyl sulfide complex, undergo conjugate addition to enones in the presence of trimethylsilyl chloride to produce γ-(phenylthio) ketones. Protection of the ketone as its dioxolane, and reductive lithiation with LDBB provides carbonyl-protected γ-lithioketones. ...