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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 21
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Original Articles

Asymmetric Synthesis. XX. Asymmetric Oxidative Coupling Reaction of Imine Carbanions via (+)-Camphor Chiral Template

Guilan Liu Chengdu Institute of Organic Chemistry, Academia sinica, Chengdu, 610015, P. R. China
,
Wenhao Hu Chengdu Institute of Organic Chemistry, Academia sinica, Chengdu, 610015, P. R. China
,
Yuzi Ma Chengdu Institute of Organic Chemistry, Academia sinica, Chengdu, 610015, P. R. China
,
Yaozhong Jiang Chengdu Institute of Organic Chemistry, Academia sinica, Chengdu, 610015, P. R. China
&
Teng-Kuei Yang Department of Chemistry, National Chung-Hsing University, Taichung, Taiwan, 40227, Republic of China
Pages 3115-3122 | Received 05 May 1994, Published online: 23 Sep 2006
 
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Abstract

The paper studies the asymmetric coupling reaction of (+)-camphor imine (5) from 2-aminomethylpyridine with a variety of oxidative coupling agents. From the coupling product (7), as determined by 1H-NMR, the threo diastereomers are isolated with 80–95% d.e. When FeCl3 or 1.2-dibromoethane is used as oxidative coupling agents, a 93:7 threo: erythro ratio with a d. e. for the threo compound of 95% is obtained.

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