Enantioselective Michael addition of malononitrile to chalcones catalyzed by a simple quinine–Al(OiPr)3 complex: a simple method for the synthesis of a chiral 4H-pyran derivative

Jian Shi; Min Wang; Ling He; Ke Zheng; Xiaohua Liu; Lili Lin; Xiaoming Feng

doi:10.1039/B908632C

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Enantioselective Michael addition of malononitrile to chalcones catalyzed by a simple quinine–Al(OⁱPr)₃ complex: a simple method for the synthesis of a chiral 4H-pyran derivative†

Jian Shi,^a Min Wang,^a Ling He,^a Ke Zheng,^a Xiaohua Liu,^a Lili Lin^a and Xiaoming Feng*^a

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* Corresponding authors

^a Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China
E-mail: xmfeng@scu.edu.cn
Fax: + 86 28 85418249
Tel: +86 28 85418249

Abstract

Enantioselective Michael addition of malononitrile to chalcones was catalyzed by a simple quinine and Al(OⁱPr)₃ complex and products were obtained in good ee as well as high yields, which facilitated the asymmetric synthesis of a biologically active 4H-pyran compound.

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Supplementary files

Experimental procedures and analytical and spectral data ofproducts PDF (2720K)

Article information

DOI: https://doi.org/10.1039/B908632C
Article type: Communication
Submitted: 30 Apr 2009
Accepted: 27 May 2009
First published: 24 Jun 2009

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Chem. Commun., 2009, 4711-4713

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Enantioselective Michael addition of malononitrile to chalcones catalyzed by a simple quinine–Al(OⁱPr)₃ complex: a simple method for the synthesis of a chiral 4H-pyran derivative

J. Shi, M. Wang, L. He, K. Zheng, X. Liu, L. Lin and X. Feng, Chem. Commun., 2009, 4711 DOI: 10.1039/B908632C

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