Tetrahedron

Direct transformation of allylic and benzylic alcohols or their silylated derivatives into organolithium compounds

E Alonso, D Guijarro, M Yus

Index: Alonso, Emma; Guijarro, David; Yus, Miguel Tetrahedron, 1995 , vol. 51, # 42 p. 11457 - 11464

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Citation Number: 24

Abstract

The reaction of allylic or benzylic alcohols 1 with n-butyllithium followed by treatment with lithium powder and a catalytic amount of DTBB (5 mol%) in THF at room temperature gives a solution of the corresponding alkyllithium reagent, which reacts in situ with different electrophiles to yield the expected products 2. Alternatively, the O-silylated derivatives of the same alcohols are lithiated under Barbier-type reaction conditions to afford the same ...