(1R,2R)-(+)-(1,2)-DPEN-Bonded Sulfonic Acid Resin: A Trifunctional Heterogeneous Catalyst for Asymmetric Michael Additions of Acetone to Nitroolefins |
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| Authors: | Chao Zhang Jing Li Jun Tian Wangwang Fang Yang Li Ligong Chen |
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| Institution: | 1. School of Chemical Engineering and Technology, Tianjin University, Tianjin, China;2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, China;3. Beijing Tiangang Auxiliary Co., Beijing, China |
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| Abstract: | Based on (1R,2R)-(+)-(1,2)-DPEN skeleton, a series of primary amine–sulfamide bifunctional catalysts were synthesized, which exhibited excellent catalytic performance in the Michael addition of acetone to β-nitrostyrene. Therefore, a trifunctional heterogeneous catalyst was designed and prepared by simple N-sulfonyl reaction of (1R,2R)-(+)-(1,2)-DPEN and sulfonyl chloride resin. It was employed for the aforementioned addition without any additive and satisfactory results (80.5% conversion; 84.3% ee) were obtained. Meanwhile, the structural and textural properties of the catalyst were characterized by infrared spectroscopy (FT-IR), elemental analysis, SEM, and N2 adsorption and desorption experiments. Finally, the generality of the catalyst was investigated. |
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| Keywords: | (1R 2R)-(+)-(1 2)-DPEN Asymmetric catalysis Michael addition trifunctional heterogeneous catalyst |
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