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 in | Chemical communications (Cambridge, England) Vol. 57; no. 40; pp. 4938 - 4941 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
18.05.2021
Royal Society of Chemistry |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1359-7345 1364-548X 1364-548X |
| DOI | 10.1039/D1CC00777G |
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| Abstract | 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). |
|---|---|
| AbstractList | 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 gamma,gamma-disubstituted butenolide moieties and adjacent quaternary-tertiary stereocenters are obtained in synthetically viable results (up to 97% yield, 77 : 23 dr and 97% ee). 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). 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). 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).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). |
| Author | Zhou, Ming-Qiang Zhang, Xia-Yan Yuan, Wei-Cheng Yuan, Shu-Pei You, Yong Jia, Yun-Qing Zhao, Jian-Qiang Wang, Zhen-Hua |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/33876161$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1021/ol061604w 10.1021/ol100014m 10.1002/slct.201601425 10.1039/b820693g 10.1002/adsc.201100577 10.1039/C7OB00413C 10.1002/ejoc.200901492 10.1021/jacs.8b13367 10.1021/cr900211p 10.1039/D0SC01914C 10.1039/b817310a 10.1002/chem.201500349 10.1039/c005345g 10.1039/C4CS00209A 10.1021/ol200939t 10.1021/cr100403z 10.1039/b923063g 10.1002/anie.200803947 10.1002/anie.200701836 10.1039/D0CC05474G 10.1021/np100599g 10.1039/b516351j 10.1039/C9CS00346K 10.1021/acs.chemrev.7b00151 10.1002/chem.201001662 10.1021/ol100161n 10.1002/ejoc.201201335 10.1021/ja067083p 10.1039/c7ob00413c 10.1039/d0ra09133b 10.1039/c4cs00209a 10.1039/c9cs00346k 10.1039/d0sc01914c 10.1039/d0cc05474g |
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| Snippet | An efficient catalytic asymmetric coupling of vinylogous species is developed
via
deconjugated butenolide addition to vinylogous imines
in situ
generated from... An efficient catalytic asymmetric coupling of vinylogous species is developed via deconjugated butenolide addition to vinylogous imines in situ generated from... |
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| SubjectTerms | Asymmetry catalysts Chemistry Chemistry, Multidisciplinary Coupling Crystallography Imines Indoles Physical Sciences Science & Technology |
| Title | Catalytic asymmetric coupling of vinylogous species via deconjugated butenolide addition to vinylogous imines in situ generated from arylsulfonyl indoles |
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