Tetrahedron

Generation, rearrangements and some synthetic uses of bishomoallyllithiums

F Chen, B Mudryk, T Cohen

Index: Chen, Fangping; Mudryk, Boguslaw; Cohen, Theodore Tetrahedron, 1994 , vol. 50, # 45 p. 12793 - 12810

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Citation Number: 28

Abstract

A general preparative method for bishomoallyllithiums consists of reductive lithiation by 4, 4′-di-tert-butylbiphenylide (LDBB) of bishomoallyl phenyl sulfides, which can be prepared by (1) thioacetalization of γ, δ-unsaturated ketones followed by replacing one of the phenylthio groups with an alkyl group or a hydrogen or (2) Wittig or Peterson olefination of γ (phenylthio) ketones prepared in turn by conjugate addition of phenylthiomethyl cuprates ...