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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Published inChemical communications (Cambridge, England) Vol. 58; no. 4; pp. 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 Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 06.01.2022
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.
Bibliography:2102386
For ESI and crystallographic data in CIF or other electronic format see DOI
2102388
10.1039/d1cc06357j
Electronic supplementary information (ESI) available: Experimental procedures, spectral data of new compounds, and crystallographic data. CCDC
and
,
2111474
2113255
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc06357j