Issue 80, 2024

One-pot synthesis of functionalized dihydropyridin-2-ones via carbene-catalyzed base-controlled [3+3] annulation reaction

Abstract

Herein, we have described a novel organocatalytic approach to access biologically important dihydropyridin-2-ones in a one-pot way with generally high yields (up to 99%) and excellent enantioselectivities (up to 99% ee). This reaction proceeded via a new dual activation mode, including in situ-generated α,β-unsaturated acylazoliums and 4-dimethylaminopyridinium salts that underwent a Michael addition/1,4-H migration/lactamization sequence. The base-triggered 4-dimethylaminopyridinium ylide formation pathway over the competing substitution reaction pathway of vicinal haloamines is noteworthy.

Graphical abstract: One-pot synthesis of functionalized dihydropyridin-2-ones via carbene-catalyzed base-controlled [3+3] annulation reaction

Supplementary files

Article information

Article type
Communication
Submitted
15 Jul 2024
Accepted
11 Sep 2024
First published
13 Sep 2024

Chem. Commun., 2024,60, 11327-11330

One-pot synthesis of functionalized dihydropyridin-2-ones via carbene-catalyzed base-controlled [3+3] annulation reaction

Z. Wang, G. Ma, Y. Xu, Q. Wang, M. Zhang, X. Ma, C. Ma, A. Sun, R. Xia and H. Liu, Chem. Commun., 2024, 60, 11327 DOI: 10.1039/D4CC03521F

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