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

doi:10.1039/C2OB26202A

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Organic & Biomolecular Chemistry

Issue 38, 2012

The international home of synthetic, physical and biomolecular organic chemistry.

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

Ying Fu,*^a Yanhua Liu,^a Yaojuan Chen,^a Helmut M. Hügel,^b Minzhu Wang,^a Danfeng Huang^a and Yulai Hu^a

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College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, An'ning East Road No. 967, Gansu Province, P.R. China
E-mail: fuying@iccas.ac.cn

Health Innovations Research Institute and School of Applied Sciences, RMIT University, Melbourne, Australia

Org. Biomol. Chem., 2012,10, 7669-7672

DOI: 10.1039/C2OB26202A
Received 24 Jun 2012, Accepted 31 Jul 2012
First published online 02 Aug 2012

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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 NH₄Cl solution.

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

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

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

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