Novel Chiral Helical Polyisocyanides Containing Cyclohexanediamine Pendants for Asymmetric Michael Addition Reaction and Aldol Reaction
Catalysis Letters, ISSN: 1572-879X, Vol: 154, Issue: 4, Page: 1420-1430
2024
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Article Description
A novel helical poly(phenylisocyanide)-supported catalyst bearing (1R,2R)-1,2-cyclohexanediamine pendant (poly-2) was synthesized. The chiral cyclohexanediamine polymer catalyst exhibited superior catalytic activity and stereoselectivity in the Michael addition reaction. The polymer poly-2 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-2 can also catalyze the Aldol reaction of p-nitrobenzaldehyde with cyclohexanone, with ee value of 49% and dr value of 60/40. Graphical Abstract: Asymmetric Michael addition reaction and Aldol reaction catalyzed by poly-2 (Figure presented.).
Bibliographic Details
Springer Science and Business Media LLC
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