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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Published inOrganic chemistry frontiers an international journal of organic chemistry Vol. 9; no. 3; pp. 660 - 666
Main Authors Xie, Ronghao, Chen, Shixiao, Xiang, Xianping, Yin, Xiangcong, Lubin, Xu, Li, Shuai-Shuai, Wang, Liang, Dong, Fengying
Format Journal Article
LanguageEnglish
Published London Royal Society of Chemistry 01.02.2022
Subjects
Aldehydes
Condensates
Construction
Hydrides
Organic chemistry
Propargyl groups
Scaffolds
Stereoselectivity
Substrates
Transesterification
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Summary: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:2052-4110
2052-4110
DOI:10.1039/d1qo01530c