Volume 46, Issue 3 pp. 389-392
Communication

Highly Asymmetric Michael Addition to α,β-Unsaturated Ketones Catalyzed by 9-Amino-9-deoxyepiquinine

Jian-Wu Xie

Jian-Wu Xie

Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province, Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, P.R. China, Fax: (+86) 28-852-239-78

Graduate School of the Chinese Academy of Sciences, Beijing, P.R. China

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Wei Chen

Wei Chen

Key laboratory of Drug-Targeting of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P.R. China, Fax: (+86) 28-85502609

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Rui Li

Rui Li

Key laboratory of Drug-Targeting of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P.R. China, Fax: (+86) 28-85502609

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Mi Zeng

Mi Zeng

Key laboratory of Drug-Targeting of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P.R. China, Fax: (+86) 28-85502609

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Wei Du

Wei Du

Key laboratory of Drug-Targeting of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P.R. China, Fax: (+86) 28-85502609

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Lei Yue

Lei Yue

Key laboratory of Drug-Targeting of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P.R. China, Fax: (+86) 28-85502609

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Ying-Chun Chen Prof. Dr.

Ying-Chun Chen Prof. Dr.

Key laboratory of Drug-Targeting of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P.R. China, Fax: (+86) 28-85502609

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Yong Wu Prof. Dr.

Yong Wu Prof. Dr.

Key laboratory of Drug-Targeting of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P.R. China, Fax: (+86) 28-85502609

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Jin Zhu Prof.

Jin Zhu Prof.

Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province, Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, P.R. China, Fax: (+86) 28-852-239-78

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Jin-Gen Deng Prof. Dr.

Jin-Gen Deng Prof. Dr.

Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province, Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, P.R. China, Fax: (+86) 28-852-239-78

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First published: 27 December 2006
Citations: 306

We are grateful for the financial support of the National Natural Science Foundation of China (20502018), the Ministry of Education (NCET-05-0781), and Sichuan University.

Graphical Abstract

Michael–Michael–retro-Michael cascade reactions are promoted by the highly efficient organocatalyst 9-amino-9-deoxyepiquinine (1). The asymmetric direct vinylogous Michael addition of α,α-dicyanoalkenes to α,β-unsaturated ketones may be followed by an intramolecular Michael addition and a retro-Michael reaction to afford polysubstituted 2-cyclohexen-1-one derivatives with high enantioselectivity (see example).

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