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January 25, 2026

Enantioselective 4 + 2 Annulation Reaction of C1-Ammonium Enolate and Azadiene for 3,4-Dihydroquinolinones Synthesis

DCDivakar ChaudharyIndian Institute of Technology Roorkee AMAkshay MinaIndian Institute of Technology Roorkee SSSunil Kumar SinghUniversity of Wisconsin–Madison

Puntos clave

The aim is to develop a practical enantioselective synthesis of dihydroquinolinones using a unique annulation process.
Utilized C1-ammonium enolate and azadiene intermediates for synthesis.
Executed an asymmetric [4 + 2] annulation reaction.
Explored postmodification techniques for derivative production.
Successfully synthesized a variety of α-arylated dihydroquinolinones.
Provided a scalable method that avoids transition metals and expensive catalysts.
Enabled further transformations into tetrahydroquinoline and other derivatives.

Resumen

Here, we describe a practical and mechanistically intriguing enantioselective synthesis of dihydroquinolinones through an asymmetric 4 + 2 annulation process utilizing an activated ester-derived transient C1-ammonium enolate and azadiene intermediates. Additionally, dihydroquinolinones may be further transformed into tetrahydroquinoline, dihydrothioquinolinones pharmacophores, and δ-amino ester building blocks through postmodification techniques. The method is practical and scalable, eliminates the use of transition metals or expensive catalysts, and provides the opportunity to access a variety of α-arylated enantioenriched dihydroquinolone and tetrahydroquinoline products with a variety of electronically diverse substituents.

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