Catalytic asymmetric coupling of vinylogous species via deconjugated butenolide addition to vinylogous imines in situ generated from arylsulfonyl indoles

An efficient catalytic asymmetric coupling of vinylogous species is developed via deconjugated butenolide addition to vinylogous imines in situ generated from arylsulfonyl indoles. With quinine-derived bifunctional squaramide as the catalyst, a series of structurally diverse enantioenriched sec -alk...

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Published inChemical communications (Cambridge, England) Vol. 57; no. 40; pp. 4938 - 4941
Main Authors Yuan, Shu-Pei, Zhang, Xia-Yan, Jia, Yun-Qing, Wang, Zhen-Hua, Zhao, Jian-Qiang, You, Yong, Zhou, Ming-Qiang, Yuan, Wei-Cheng
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 18.05.2021
Royal Society of Chemistry
Subjects
Asymmetry
catalysts
Chemistry
Chemistry, Multidisciplinary
Coupling
Crystallography
Imines
Indoles
Physical Sciences
Science & Technology
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ISSN1359-7345
1364-548X
1364-548X
DOI10.1039/D1CC00777G

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Summary:An efficient catalytic asymmetric coupling of vinylogous species is developed via deconjugated butenolide addition to vinylogous imines in situ generated from arylsulfonyl indoles. With quinine-derived bifunctional squaramide as the catalyst, a series of structurally diverse enantioenriched sec -alkyl-3-substituted indoles containing valuable γ,γ -disubstituted butenolide moieties and adjacent quaternary-tertiary stereocenters are obtained in synthetically viable results (up to 97% yield, 77 : 23 dr and 97% ee).
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/D1CC00777G