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Organocatalytic inverse-electron-demand Diels-Alder reaction between 5-alkenyl thiazolones and β,γ-unsaturated carbonyl compounds.

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An inverse-electron-demand oxa-Diels-Alder reaction of 5-alkenyl thiazolones with β,γ-unsaturated carbonyl compounds enabled by quinine thiourea was studied, which allows the enantioselective synthesis of a broad range of highly functionalized pyranthiazoles… Click to show full abstract

An inverse-electron-demand oxa-Diels-Alder reaction of 5-alkenyl thiazolones with β,γ-unsaturated carbonyl compounds enabled by quinine thiourea was studied, which allows the enantioselective synthesis of a broad range of highly functionalized pyranthiazoles bearing three continuous stereocenters. This protocol is adaptable to a wide scope of substrates and has great potential for scale-up synthesis and facile transformation.

Keywords: alkenyl thiazolones; diels alder; reaction alkenyl; inverse electron; alder reaction; electron demand

Journal Title: Chemical communications
Year Published: 2022

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