Diastereoselective Synthesis of 2-(Pyrrolidin-2-ylidene)-1H-indene-1,3-diones via 1,3-Dipolar Cycloaddition of H-Bond-Assisted Azomethine Ylides with Chalcones

Abstract

The diastereoselective synthesis of NH-unprotected pyrrolidin-2-ylidene derivatives was accomplished via 1,3-dipolar cycloaddition of H-bond-assisted azomethine ylides with chalcones. This process resulted in the formation of three stereogenic centers, exhibiting excellent diastereoselectivity. The effectiveness of this approach was illustrated through a gram-scale experiment, and the structure of the final product was confirmed by single-crystal X-ray analysis.

Key words

diastereoselective synthesis - pyrrolidin-2-ylidenes - Huisgen reaction - ninhydrin - chalcones

Publication History

Received: 30 December 2024

Accepted after revision: 11 March 2025

Article published online:
22 April 2025

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