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Isothiourea and Brønsted Acid Cooperative Catalysis: Enantioselective Construction of Dihydropyridinones

Yu‐Chen Zhang, Rui‐Long Geng, Jin Song, Liu‐Zhu Gong

2020Organic Letters34 citationsDOI

Abstract

Asymmetric annulation of bench-stable α,β-unsaturated aryl esters with enamines was realized via cooperative catalysis of chiral isothiourea and Brønsted acid. This reaction proceeds via a chiral α,β-unsaturated acyl ammonium intermediate and offers a rapid access to functionalized 3,4-dihydropyridin-2-ones in high yields and excellent enantioselectivities.

Topics & Concepts

ChemistryEnantioselective synthesisBrønsted–Lowry acid–base theoryCatalysisAnnulationAmmoniumArylCombinatorial chemistryOrganic chemistryOrganocatalysisReaction conditionsAlkylAsymmetric Synthesis and CatalysisSynthesis and Catalytic ReactionsSynthetic Organic Chemistry Methods
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