Catalytic asymmetric aromatizing inverse electron-demand [4+2] cycloaddition of 1-thioaurones and 1-azaaurones

Using 1-thioaurones and 1-azaaurones as electron-deficient oxa-dienes, an organocatalytic asymmetric aromatizing inverse electron-demand [4+2] cycloaddition with γ-deconjugated butenolides and azlactones was developed. A wide range of optically active benzothiophene-fused δ-lactones and indole-fused...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-01, Vol.58 (4), p.553-556
Main Authors: Yuan, Shu-Pei, Dou, Pei-Hao, Jia, Yun-Qing, Zhao, Jian-Qiang, You, Yong, Wang, Zhen-Hua, Zhou, Ming-Qiang, Yuan, Wei-Cheng
Format: Article
Language:English
Subjects:
Asymmetry
Benzothiophene
Cycloaddition
Dienes
Electrons
Lactones
Optical activity
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Summary:Using 1-thioaurones and 1-azaaurones as electron-deficient oxa-dienes, an organocatalytic asymmetric aromatizing inverse electron-demand [4+2] cycloaddition with γ-deconjugated butenolides and azlactones was developed. A wide range of optically active benzothiophene-fused δ-lactones and indole-fused δ-lactones were obtained with desirable outcomes (up to 94% yield, >99 : 1 dr and 99% ee). An organocatalytic asymmetric aromatizing inverse electron-demand [4+2] cycloaddition of 1-thioaurones/1-azaaurones with γ-deconjugated butenolides and azlactones was developed.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc06357j