Issue 10, 2012
From the journal:

Organic & Biomolecular Chemistry

Catalytic effect and recyclability of imidazolium-tagged bis(oxazoline) based catalysts in asymmetric Henry reactions†

Zhi-Ming Zhou,*ab   Zhi-Huai Li,a   Xiao-Yan Hao,a   Jun Zhang,a   Xiao Dong,a   Ying-Qiang Liu,a   Wen-Wen Sun,a   Dan Caoa  and  Jin-Liang Wanga  

* Corresponding authors

a R&D Centre for Pharmaceuticals, School of Chemical Engineering and the Environment, Beijing Institute of Technology, Beijing, PR China
E-mail: zzm@bit.edu.cn
Fax: +86 010 68912664
Tel: +86 010 68912664

b State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing, PR China

Abstract

Functional imidazolium ionic liquids have been developed as a new class of versatile catalysts. C2-symmetric imidazolium-tagged bis(oxazoline) ligands were prepared, and the anions of the ligands were altered. The catalysts based on the new ligands and Cu(OAc)2·H2O were applied in asymmetric Henry reactions between various aldehydes 3 and CH3NO24. The catalysts achieved a high level of enantioselectivity; product (R)-5n was attained at 94% ee in MeOH. Moreover, the catalyst could be recycled 6 times without an obvious loss of activity or enantioselectivity. In addition, a theoretical mechanistic study was conducted to explain the origin of the enantioselectivity.

Graphical abstract: Catalytic effect and recyclability of imidazolium-tagged bis(oxazoline) based catalysts in asymmetric Henry reactions

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Article information

DOI
https://doi.org/10.1039/C2OB06434K
Article type
Paper
Submitted
22 Aug 2011
Accepted
05 Dec 2011
First published
07 Dec 2011

Org. Biomol. Chem., 2012,10, 2113-2118

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Catalytic effect and recyclability of imidazolium-tagged bis(oxazoline) based catalysts in asymmetric Henry reactions

Z. Zhou, Z. Li, X. Hao, J. Zhang, X. Dong, Y. Liu, W. Sun, D. Cao and J. Wang, Org. Biomol. Chem., 2012, 10, 2113 DOI: 10.1039/C2OB06434K

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