Asymmetric Addition of Organolithium Reagents to Ferrocenylimines

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (04): 601-605. Previous Articles Next Articles

Original Articles

有机锂试剂对二茂铁亚胺的不对称加成反应

张慧卿; 袁浩 ; 周智明*

(北京理工大学化工与环境学院北京 100081)

收稿日期:2008-05-05 修回日期:2008-10-17 发布日期:2009-04-20
通讯作者: 周智明

Asymmetric Addition of Organolithium Reagents to Ferrocenylimines

Zhang, Huiqing; Yuan, Hao ; Zhou, Zhiming*

(School of Chemical Engineering & the Environment, Beijing Institute of Technology, Beijing 100081)

Received:2008-05-05 Revised:2008-10-17 Published:2009-04-20
Contact: Zhou, Zhiming

Abstract

The (－)-sparteine-mediated enantioselective addition of organolithium compounds to achiral ferrocenylimines and diastereoselective addition of organolithium reagents to chiral ferrocenyl imines de-rived from inexpensive (R)- and (S)-1-phenylethylamines were carried out. The influence of the imine struc-ture, as well as the effect of experimental conditions on the reaction was studied. Modest enantiomeric ex-cess was obtained with the achiral imines. And high diastereoselectivity was achieved with the chiral imine derived from (R)-(＋)-1-phenylethylamine in the presence of the Lewis acid BF3•OEt2.

Key words: ferrocenylimine, (－)-sparteine, asymmetric addition, Lewis acid

Cite this article

Zhang, Huiqing; Yuan, Hao ; Zhou, Zhiming*. Asymmetric Addition of Organolithium Reagents to Ferrocenylimines[J]. Chin. J. Org. Chem., 2009, 29(04): 601-605.

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有机锂试剂对二茂铁亚胺的不对称加成反应

Asymmetric Addition of Organolithium Reagents to Ferrocenylimines

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