Issue 11, 2023

Palladium-catalyzed asymmetric (4 + 3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines: access to optically active spirooxindoles

Abstract

A palladium-catalyzed asymmetric (4 + 3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines with 2-methylidenetrimethylene carbonate was reported to enantioselectively afford trifluoromethylated spirooxindoles in moderate yields and good to excellent ee values. Experimentally, the reaction proceeded smoothly in the absence of a Brønsted base in a one-pot manner, which paved a way for efficient and cost-effective construction of optically pure trifluoromethylated medium-sized rings.

Graphical abstract: Palladium-catalyzed asymmetric (4 + 3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines: access to optically active spirooxindoles

Supplementary files

Article information

Article type
Research Article
Submitted
05 Apr 2023
Accepted
15 Apr 2023
First published
19 Apr 2023

Org. Chem. Front., 2023,10, 2648-2652

Palladium-catalyzed asymmetric (4 + 3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines: access to optically active spirooxindoles

Y. Meng, M. Song, Y. Wang, Y. Wang and E. Li, Org. Chem. Front., 2023, 10, 2648 DOI: 10.1039/D3QO00501A

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