Issue 36, 2023

Base-promoted Conia-ene cyclization of propargyl amides

Abstract

We report a tBuOK-promoted synthesis of 1,3-dihydro-2H-pyrrol-2-one and 4-methylenepyrrolidin-2-one systems via Conia-ene like intramolecular cyclization. The method features extremely short reaction times (5 min) and mild reaction conditions (rt), enabling the trapping of a propargyl unit by an amide enolate. An intriguing anionic chain mechanism is at work, which can trigger the isomerization of an exo-alkene giving access to the otherwise elusive endo-product.

Graphical abstract: Base-promoted Conia-ene cyclization of propargyl amides

Supplementary files

Article information

Article type
Communication
Submitted
11 Jul 2023
Accepted
28 Aug 2023
First published
29 Aug 2023

Org. Biomol. Chem., 2023,21, 7311-7315

Base-promoted Conia-ene cyclization of propargyl amides

A. Cerveri, M. Vettori, A. Serafino and G. Maestri, Org. Biomol. Chem., 2023, 21, 7311 DOI: 10.1039/D3OB01107K

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