The Squaramide-Catalyzed 1,3-Dipolar Cycloaddition of Nitroalkenes with N-2,2,2-Trifluoroethylisatin Ketimines: An Approach for the Synthesis of 5′-Trifluoromethyl-spiro[pyrrolidin-3,2′-oxindoles]

A Cinchona alkaloid‐derived squaramide‐catalyzed asymmetric cycloaddition of trfluoromethyl‐containing azomethine ylides with β‐nitroalkenes was realized under mild conditions. A series of biologically important 5′‐trifluoromethyl‐ spiro[pyrrolidin‐3,2′‐oxindoles] was synthesized efficiently by this...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2015-10, Vol.357 (14-15), p.3187-3196
Main Authors: Sun, Quantao, Li, Xiaoyuan, Su, Jinhuan, Zhao, Long, Ma, Mingxia, Zhu, Yuanyuan, Zhao, Yanyan, Zhu, Ranran, Yan, Wenjin, Wang, Kairong, Wang, Rui
Format: Article
Language:English
Subjects:
1,3‐dipolar cycloaddition
2′-oxindoles
3-dipolar cycloaddition
5′-trifluoromethyl-spiro-[pyrrolidin-3
5′‐trifluoromethyl‐spiro‐[pyrrolidin‐3,2′‐oxindoles]
Asymmetry
Catalysis
Cycloaddition
Imines
squaramides
Synthesis
trifluoromethyl-containing azomethine ylides
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Summary:A Cinchona alkaloid‐derived squaramide‐catalyzed asymmetric cycloaddition of trfluoromethyl‐containing azomethine ylides with β‐nitroalkenes was realized under mild conditions. A series of biologically important 5′‐trifluoromethyl‐ spiro[pyrrolidin‐3,2′‐oxindoles] was synthesized efficiently by this process in excellent yields, enantioseletivities and diastereoselectivities.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201500416