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Construction of Adjacent Quaternary and Tertiary Stereocenters by Conjugate Addition Using Polymer-Supported Cinchona Alkaloids as Catalysts

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Abstract

A series of polymer-bound cinchona alkaloids has been prepared. The resultant polymer-bound cinchona alkaloids have been used as the catalysts for the asymmetric Michael reaction of 1,3-dicarbonyl compounds and N-benzylmaleimide. The corresponding asymmetric Michael addition product, the first example of adjacent quaternary and tertiary stereocenters synthesized in the presence of a polymer-bound catalyst, has a selectivity of up to 86% ee. Besides, immobilized alkaloid V retains stereochemical reactivity even after being recycled for six times.

Graphical Abstract

A series of polymer-bound cinchona alkaloids has been prepared. The resultant polymer-bound cinchona alkaloids have been used as the catalysts for the asymmetric Michael reaction of 1,3-dicarbonyl compounds and N-benzylmaleimide. The corresponding asymmetric Michael addition product, the first example of adjacent quaternary and tertiary stereocenters synthesized in the presence of a polymer-bound catalyst, has a selectivity of up to 86% ee. Besides, immobilized alkaloid V retains stereochemical reactivity even after being recycled for six times.

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Acknowledgments

We are grateful to the Natural Science Foundation of Henan Province for the financial support (No. 2008A150003).

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Authors and Affiliations

  1. Key Laboratory of Ministry of Education for Special Functional Materials, Henan University, 475004, Kaifeng, China

    Yanyan Qin & Yuanchen Cui

  2. College of Chemistry and Chemical Engineering, Henan University, 475004, Kaifeng, China

    Yanyan Qin, Gengxu Yang, Lili Yang & Jia Li

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  1. Yanyan Qin
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  2. Gengxu Yang
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  3. Lili Yang
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  4. Jia Li
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  5. Yuanchen Cui
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Correspondence to Yuanchen Cui.

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Qin, Y., Yang, G., Yang, L. et al. Construction of Adjacent Quaternary and Tertiary Stereocenters by Conjugate Addition Using Polymer-Supported Cinchona Alkaloids as Catalysts. Catal Lett 141, 481–488 (2011). https://doi.org/10.1007/s10562-010-0509-7

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