Journal
CHEMICAL COMMUNICATIONS
Volume 57, Issue 40, Pages 4938-4941Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc00777g
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Funding
- National Key R&D Program of China [2018YFC0807301-3]
- National NSFC [21901024, 21871252, 21801024, 21801026]
- Material Evidence Identification Center of Ministry of Public Security [2019CSEEKFKT06]
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An efficient catalytic asymmetric coupling of vinylogous species is developed by adding deconjugated butenolide to vinylogous imines in situ generated from arylsulfonyl indoles. Using 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 with 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 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).
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