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250. Chem. Commun., 2022, 58, 4227-4230

date:2022-03-20

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

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


https://doi.org/10.1039/D2CC00457G





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.

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