Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels–Alder Reaction of Dioxopyrrolidines with Hetero-Substituted Alkenes

Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels–Alder Reaction of Dioxopyrrolidines with Hetero-Substituted Alkenes

A highly efficient enantioselective inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with heterosubstituted alkenes has been realized by using a N,N′-dioxide/Ni­(II) complex as the catalyst. A series of chiral bicyclic dihydropyranes were generated in excellent yields, good d...

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Veröffentlicht in:Journal of organic chemistry 2018-08, Vol.83 (15), p.8679-8687
Hauptverfasser: Hu, Xinyue, zhou, Yuhang, Lu, Yan, Zou, Sijia, Lin, Lili, Liu, Xiaohua, Feng, Xiaoming
Format: Artikel
Sprache:eng
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Zusammenfassung:A highly efficient enantioselective inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with heterosubstituted alkenes has been realized by using a N,N′-dioxide/Ni­(II) complex as the catalyst. A series of chiral bicyclic dihydropyranes were generated in excellent yields, good dr, and excellent ee values. Besides, a catalytic cycle with a possible transition state was proposed.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00839