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Enantio- and diastereoselective synthesis of spiropyrazolones via an organocatalytic [1 + 2 + 3] multicomponent reaction

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Abstract

An asymmetric catalytic multicomponent reaction of malononitrile, benzaldehyde, and α-arylidene pyrazolinones to produce spiropyrazolones has been reported. The [1 + 2 + 3] multicomponent reaction was catalyzed by chiral cinchona alkaloids to provide spiropyrazolones in high yields, with excellent enantioselectivities and good diastereoselectivities. We also performed control experiments and proposed a plausible catalytic cycle based on the observed experimental results to explain the reaction process and stereoselectivity of the asymmetric multicomponent reaction.

Graphical abstract: Enantio- and diastereoselective synthesis of spiropyrazolones via an organocatalytic [1 + 2 + 3] multicomponent reaction

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Publication details

The article was received on 02 Sep 2019, accepted on 28 Sep 2019 and first published on 30 Sep 2019


Article type: Paper
DOI: 10.1039/C9OB01927H
Org. Biomol. Chem., 2019, Advance Article

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    Enantio- and diastereoselective synthesis of spiropyrazolones via an organocatalytic [1 + 2 + 3] multicomponent reaction

    Y. Ji, H. Li, Y. Ai, G. Li, X. He, W. Huang, R. Huang and B. Han, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01927H

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