Issue 41, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
02 Sep 2019
Accepted
28 Sep 2019
First published
30 Sep 2019

Org. Biomol. Chem., 2019,17, 9217-9225

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, 17, 9217 DOI: 10.1039/C9OB01927H

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