Issue 38, 2012
From the journal:

Organic & Biomolecular Chemistry

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 Huanga  and  Yulai Hua  

* Corresponding authors

a 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

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

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 NH4Cl solution.

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

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Article information

DOI
https://doi.org/10.1039/C2OB26202A
Article type
Communication
Submitted
24 Jun 2012
Accepted
31 Jul 2012
First published
02 Aug 2012

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

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

Y. Fu, Y. Liu, Y. Chen, H. M. Hügel, M. Wang, D. Huang and Y. Hu, Org. Biomol. Chem., 2012, 10, 7669 DOI: 10.1039/C2OB26202A

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