Synthesis of Chiral Spiro[oxindole-3,2′-pyrrolidine] Derivatives Integrated with Spiro Indane-1,3-dione and Trifluoromethyl Group Pharmacophores via Organocatalyzed Asymmetric [3+2] Annulation

Abstract

A mild and efficient organocatalyzed [3+2] cycloaddition of isatin-derived ketimines and 2-ylideneindane-1,3-diones has been realized. The resulting spiro[oxindole-3,2′-pyrrolidine]s bearing both a spiro indane-1,3-dione motif and a trifluoromethyl group were obtained in high yields with good diastereo- and enantioselectivities.

Key words

asymmetric synthesis - indane-1,3-dione - isatin-based ketimine - organocatalysis - spiro[oxindole-3,2′-pyrrolidine]

Publication History

Received: 14 October 2022

Accepted after revision: 06 December 2022

Accepted Manuscript online:
06 December 2022

Article published online:
10 January 2023

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