Tetrahedron

Isoprene-catalysed lithiation: deprotection and functionalisation of imidazole derivatives

R Torregrosa, IM Pastor, M Yus

Index: Torregrosa, Rosario; Pastor, Isidro M.; Yus, Miguel Tetrahedron, 2007 , vol. 63, # 4 p. 947 - 952

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Citation Number: 16

Abstract

The isoprene-catalysed lithiation of different 1-substituted imidazoles (1)(such as trityl, allyl, benzyl, vinyl, N, N-dimethylsulfamoyl, para-toluenesulfonyl, tert-butoxycarbonyl, acetyl, trimethylsilyl, tert-butyldimethylsilyl derivatives) leads to the cleavage of the protecting group producing 1H-imidazole. The use of 1-(diethoxymethyl) imidazole (3) in the same lithiation reaction allows the preparation of the corresponding 2-lithio intermediate, which by ...