Diastereoselective construction of structurally diverse 2,3-dihydroquinolin-4-one scaffolds via redox neutral cascade [1,7]-hydride transfer/cyclization

The pharmaceutically significant 2,3-dihydroquinolin-4-one scaffolds were constructed diastereoselectively and facilely via redox-neutral cascade Knoevengel condensation/[1,7]-hydride transfer/cyclization/transesterification in DCE from readily available methyl 2-aminobenzoacetate and diverse aldehy...

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Veröffentlicht in:Organic Chemistry Frontiers 2022-02, Vol.9 (3), p.660-666
Hauptverfasser: Xie, Ronghao, Chen, Shixiao, Xiang, Xianping, Yin, Xiangcong, Xu, Lubin, Li, Shuai-Shuai, Wang, Liang, Dong, Fengying
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Sprache:eng
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Zusammenfassung:The pharmaceutically significant 2,3-dihydroquinolin-4-one scaffolds were constructed diastereoselectively and facilely via redox-neutral cascade Knoevengel condensation/[1,7]-hydride transfer/cyclization/transesterification in DCE from readily available methyl 2-aminobenzoacetate and diverse aldehydes, which features novel and highly valuable product structures, diastereoselective construction of all-carbon quaternary centers carrying allylic or propargyl groups as well as a privileged 3-spirocyclic 3,4-dihydrocoumarin moiety, an unusual pattern of [1,7]-hydride transfer, broad substrate scope, etc .
ISSN:2052-4129
2052-4110
2052-4129
2052-4110
DOI:10.1039/D1QO01530C