Trimethylsilyl chloride promoted synthesis of α-branched amines by nucleophilic addition of organozinc halides to nitronesElectronic supplementary information (ESI) available: experimental details, synthesis and characterisation of products. See DOI: 10.1039/c2ob26202a

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. Trimethylsilyl chloride acts both an indispensable reaction promoter and a ready hydroxylamine protective agent in the nucleophilic addition of organozinc reagents with nitrones.