Issue 1, 2024

DBU-catalyzed diastereoselective 1,3-dipolar [3+2] cycloaddition of trifluoroethyl amine-derived isatin ketimines with chalcones: synthesis of 5′-CF3-substituted 3,2′-pyrrolidinyl spirooxindoles

Abstract

A diastereoselective 1,3-dipolar cycloaddition reaction between trifluoroethyl amine-derived isatin ketimines and chalcones was successfully achieved in the presence of DBU. A series of 5′-CF3-substituted 3,2′-pyrrolidinyl spirooxindoles were efficiently synthesized with high yields and excellent diastereoselectivities (up to 89% yield, and >99 : 1 dr). The in vitro anticancer activities of these highly functionalized spiro[pyrrolidin-3,2′-oxindole] derivatives were evaluated.

Graphical abstract: DBU-catalyzed diastereoselective 1,3-dipolar [3+2] cycloaddition of trifluoroethyl amine-derived isatin ketimines with chalcones: synthesis of 5′-CF3-substituted 3,2′-pyrrolidinyl spirooxindoles

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Article information

Article type
Paper
Submitted
28 Nov 2023
Accepted
11 Dec 2023
First published
02 Jan 2024
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2024,14, 548-551

DBU-catalyzed diastereoselective 1,3-dipolar [3+2] cycloaddition of trifluoroethyl amine-derived isatin ketimines with chalcones: synthesis of 5′-CF3-substituted 3,2′-pyrrolidinyl spirooxindoles

F. Zhou, B. Zhu, Z. Huang, N. Lin and Z. Zhang, RSC Adv., 2024, 14, 548 DOI: 10.1039/D3RA08127C

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