Organic & Biomolecular Chemistry 2012-10-14

Trimethylsilyl chloride promoted synthesis of α-branched amines by nucleophilic addition of organozinc halides to nitrones.

Ying Fu, Yanhua Liu, Yaojuan Chen, Helmut M Hügel, Minzhu Wang, Danfeng Huang, Yulai Hu

Index: Org. Biomol. Chem. 10(38) , 7669-72, (2012)

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Abstract

A general procedure for the nucleophilic addition of organozinc halides with nitrones in the presence of trimethylsilyl chloride has been developed. Trimethylsilyl chloride was found to be both an indispensable reaction promoter and a ready hydroxylamine protective agent in these reactions. The produced O-(trimethylsilyl)hydroxylamines can be easily reduced into corresponding amines just by a zinc-copper couple in saturated aqueous NH(4)Cl solution.