Enantioselective Synthesis of Unsymmetrical Ferrocenenylamides with Planar Chirality by (－)-Sparteine Mediated Directed or-tho-Lithiation

Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (11): 1754-1758. Previous Articles Next Articles

Notes

(－)-Sparteine辅助的邻位锂化反应对映选择性合成具有平面手性的非对称二茂铁胺

周智明*^,1，袁浩^1，Snieckus, Victor ²

(¹北京理工大学化工与环境学院北京 100081)
(² Department of Chemistry, Queen s University, Kingston ON KL7 3N6, Canada)

收稿日期:2009-12-15 修回日期:2010-04-07 发布日期:2010-06-22
通讯作者: 周智明 E-mail:zzm@bit.edu.cn
基金资助:
国家自然科学基金

Enantioselective Synthesis of Unsymmetrical Ferrocenenylamides with Planar Chirality by (－)-Sparteine Mediated Directed or-tho-Lithiation

Zhou Zhiming*^{,1 Yuan Hao¹ Snieckus Victor²}

(¹School of Chemical Engineering & the Environment, Beijing Institute of Technology, Beijing 100081)
(²Department of Chemistry, Queen s University, Kingston ON KL7 3N6, Canada)

Received:2009-12-15 Revised:2010-04-07 Published:2010-06-22

Abstract

The unsymmetrical ferrocene substrate, {[N-ethyl-N-(1-methylethyl)-amino]-carbonyl}-ferro- cene, was used in (－)-sparteine me-diated directed ortho-lithiation to prepare the planer chiral ferrocene ligands. High yields and enati-oselectivities were obtained. Increased enatioinductions were observed in research work by introducing the unsymmetrical N-ethyl-N-(1-methylethyl)-carboxamide group. Moreover, crystal structure of the compound 1-{[N-ethyl-N-(1-methylethyl)-amino]carbonyl}-2-iodo-ferrocene (10a), was detected by X-ray single-crystal diffraction. The absolute configuration was determined as R for the planar chirality.

Key words: (－)-sparteine, directed ortho-lithiation, unsymmetrical ferroceylamide, planer chirality, crystal structure

Cite this article

ZHOU Zhi-Ming, YUAN Hao, Snieckus Victor. Enantioselective Synthesis of Unsymmetrical Ferrocenenylamides with Planar Chirality by (－)-Sparteine Mediated Directed or-tho-Lithiation[J]. Chin. J. Org. Chem., 2010, 30(11): 1754-1758.

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(－)-Sparteine辅助的邻位锂化反应对映选择性合成具有平面手性的非对称二茂铁胺

Enantioselective Synthesis of Unsymmetrical Ferrocenenylamides with Planar Chirality by (－)-Sparteine Mediated Directed or-tho-Lithiation

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