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Issue 5, 2020
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Organo-catalyzed asymmetric cascade annulation reaction for the construction of bi-spirocyclic pyrazolone and oxindole derivatives

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Abstract

A bifunctional organocatalyst catalyzed tandem annulation reaction between β,γ-unsaturated α-ketoesters with α-arylidene pyrazolinones was reported. The tandem Michael–aldol process allows access to optically active bi-spirocyclic pyrazolone and oxindole compounds in high yields with good to excellent enantioselectivity and diastereoselectivity. The resulting bi-spirocyclic compounds possess highly dense functionalized substituents, two all-carbon spiro quaternary stereocenters and one hemiketal stereogenic centers.

Graphical abstract: Organo-catalyzed asymmetric cascade annulation reaction for the construction of bi-spirocyclic pyrazolone and oxindole derivatives

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Article information


Submitted
03 Jan 2020
Accepted
05 Feb 2020
First published
07 Feb 2020

Org. Chem. Front., 2020,7, 796-809
Article type
Research Article

Organo-catalyzed asymmetric cascade annulation reaction for the construction of bi-spirocyclic pyrazolone and oxindole derivatives

B. Sun, J. Chen, J. Zhang, X. Yang, H. Lv, Z. Wang and X. Wang, Org. Chem. Front., 2020, 7, 796
DOI: 10.1039/D0QO00001A

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