Issue 12, 2013
From the journal:

RSC Advances

Imidazolium chiral ionic liquid derived carbene-catalyzed conjugate umpolung for synthesis of γ-butyrolactones†

Feng-Li Yu,a   Jia-Jia Jiang,a   Dong-Mei Zhao,a   Cong-Xia Xie*a  and  Shi-Tao Yub  

* Corresponding authors

a State Key Laboratory Base of Eco-chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, P. R. China
E-mail: xiecongxia@126.com
Fax: +86 532 8402 3927
Tel: +86 532 8402 3927

b College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, P. R. China
E-mail: yushitaoqust@126.com

Abstract

A serial of imidazolium chiral ionic liquids starting from commercially available (−)-menthol as a chiral pool have been synthesized and successfully used for catalyzing conjugate umpolung of α,β-unsaturated aldehydes to stereoselectively synthesize γ-butyrolactones. The catalytic activities of these ionic liquids are examined and compared. The reaction of trans-cinnamaldehyde and p-methoxycarbonyl benzaldehyde as a model has been investigated in detail, and the reaction conditions have been optimized. Under the selected conditions, the ionic liquid catalyst can catalyze the annulations of trans-cinnamaldehyde with different aromatic aldehydes to afford differently substituted γ-butyrolactones. The recyclability of the ionic liquid catalyst is investigated, and the results have indicated that the catalyst can be recycled six times without obvious activity decreasing.

Graphical abstract: Imidazolium chiral ionic liquid derived carbene-catalyzed conjugate umpolung for synthesis of γ-butyrolactones

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Article information

DOI
https://doi.org/10.1039/C3RA40211H
Article type
Paper
Submitted
14 Jan 2013
Accepted
14 Jan 2013
First published
17 Jan 2013

RSC Adv., 2013,3, 3996-4000

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Imidazolium chiral ionic liquid derived carbene-catalyzed conjugate umpolung for synthesis of γ-butyrolactones

F. Yu, J. Jiang, D. Zhao, C. Xie and S. Yu, RSC Adv., 2013, 3, 3996 DOI: 10.1039/C3RA40211H

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