Bi(OTf)3-Catalyzed Diastereoselective Three-Component Povarov Reaction of Aminoquinones toward Tetrahydroquinolinequinones.

Authors

Guixuan Zhao, Shaozhong Wang

Published in

The Journal of organic chemistry. Oct 28, 2026. Epub Oct 28, 2026.

Abstract

We have developed a Bi(OTf)3-catalyzed three-component Povarov reaction of aminoquinones, aldehydes, and olefins that provides straightforward, one-step access to highly substituted 1,2,3,4-tetrahydroquinolinequinones in isolated yields of up to 96%, with diastereoselectivities ranging from 1.6:1 to >20:1. Mechanistic studies using E- and Z-alkene probes support a stepwise cationic pathway rather than a concerted cycloaddition, which rationalizes the observed stereochemical outcomes. The synthetic utility is further highlighted by subsequent oxidative dehydrogenation to afford quinolinequinone derivatives, a class of molecules of significant biological relevance.

PMID:
42946390
Bibliographic data and abstract were imported from PubMed on 28 Oct 2026.

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