Tetrahedron letters

Highly selective γ-alkylation of triisopropylsilylallyl anion. Synthesis of α-triisopropylsilyl aldehydes.

JM Muchowski, R Naef, ML Maddox

Index: Muchowski, Joseph M.; Naef, Reto; Maddox, Michael L. Tetrahedron Letters, 1985 , vol. 26, # 44 p. 5375 - 5378

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Citation Number: 40

Abstract

Abstract The reaction of triisopropylsilylallyllithium with alkyl halides took place with considerably greater γ-selectivity than reported for trimethylsilyl allyllithium. Silica gel induced rearrangement of the epoxides 5 derived from the alkylation products 3 gave α- triisopropylsilyl aldehydes 6 by a process in which silyl group transposition occurred with predominant inversion at the migration terminus.

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