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Novel Chiral Helical Polyisocyanides Containing Cyclohexanediamine Pendants for Asymmetric Michael Addition Reaction and Aldol Reaction

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Abstract

A novel helical poly(phenylisocyanide)-supported catalyst bearing (1R,2R)-1,2-cyclohexanediamine pendant (poly-2m) was synthesized. The chiral cyclohexanediamine polymer catalyst exhibited superior catalytic activity and stereoselectivity in the Michael addition reaction. The polymer poly-2200 catalyzed the Michael addition reaction of cyclohexanone with trans-nitrosostyrene in methanol at the presence of benzoic acid with an enantiomeric excess (ee) value up to 97% and diastereoselectivity (dr) value of 79/21. In addition, the chiral polymer catalyst can be recycled for 3 times in the asymmetric Michael addition reaction without significantly lossing the catalytic activity of the catalyst. Moreover, the chiral cyclohexanediamine catalyst poly-2200 can also catalyze the Aldol reaction of p-nitrobenzaldehyde with cyclohexanone, with ee value of 49% and dr value of 60/40.

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Asymmetric Michael addition reaction and Aldol reaction catalyzed by poly-2m

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Funding

This work was supported by the Natural Science Foundation of Ningxia Province (Grant Number 2022AAC03249), the National Natural Science Foundation of China (NSFC, Nos. 52263022), the Graduate Student Innovation Project of North Minzu University (Grant Number YCX22161), the Scientific Research Start-up Project for Recruitment Talents of North Minzu University in 2020 (Grant Number 2020KYQD11). The author would like to Prof. Zong-Quan Wu of the College of Chemistry at Jilin University for his guidance during my three years of study.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, North Minzu University, Ningxia, Yinchuan, 750021, China

    Chonglong Li, Murong Zhan, Zixuan Wang, Hua Gao, Yu Yang & Hongqian Gou

  2. National Civil Affairs Commission Key Laboratory of Chemical Technology, Ningxia, Yinchuan, 750021, China

    Chonglong Li

  3. Ningxia Key Laboratory of Solar Energy Chemical Conversion Technology, Ningxia, Yinchuan, 750021, China

    Chonglong Li

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  1. Chonglong Li
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Correspondence to Chonglong Li.

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Li, C., Zhan, M., Wang, Z. et al. Novel Chiral Helical Polyisocyanides Containing Cyclohexanediamine Pendants for Asymmetric Michael Addition Reaction and Aldol Reaction. Catal Lett 154, 1420–1430 (2024). https://doi.org/10.1007/s10562-023-04423-x

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