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

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 excelle...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2020-03, Vol.7 (5), p.796-809
Main Authors: Bing-Bing Sun, Jun-Bo, Chen, Jun-Qi, Zhang, Xiao-Peng, Yang, Hao-Peng, Lv, Wang, Zheng, Xing-Wang, Wang
Format: Article
Language:English
Subjects:
Aldehydes
Chemical reactions
Crystallography
Enantiomers
Ketoesters
Optical activity
Organic chemistry
Pyrazolones
Stereoselectivity
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/d0qo00001a