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

Yang, Kai-Xuan; Ji, Dong-Sheng; Zheng, Haixue; Gu, Yucheng; Xu, Peng-Fei

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

2022

Yang, Kai-Xuan | Ji, Dong-Sheng | Zheng, Haixue | Gu, Yucheng | Xu, Peng-Fei

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.

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