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Highly Enantioselective Control of Dynamic Cascade Transformations by Dual Catalysis: Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences. Stockholm Univ, Berzelii Ctr EXSELENT, SE-10691 Stockholm, Sweden.ORCID iD: 0000-0002-5108-6487
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
Department of Materials and Environmental Chemistry, Stockholm University, Stockholm, Sweden .
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2015 (English)In: ACS Catalysis, ISSN 2155-5435, Vol. 5, no 2, 1266-1272 p.Article in journal (Refereed) Published
Abstract [en]

The highly enantioselective (up to >99.5:0.5 er) synthesis of polysubstituted spirocyclic oxindoles with four new contiguous stereocenters, including the spiro all-carbon quaternary center, is disclosed. It is accomplished by the highly stereoselective control of a dynamic conjugate/intramolecular allylic alkylation relay sequence based on the synergistic cooperation of metal and chiral amine catalysts in which the careful selection of organic Nand, metal complex, and chiral amine is essential. The intermolecular C-C bond-forming step occurred only when both the metal and chiral amine catalysts were present.

Place, publisher, year, edition, pages
2015. Vol. 5, no 2, 1266-1272 p.
Keyword [en]
all-carbon quaternary stereocenter, asymmetric cocatalysis, dynamic transformations, polysubstituted, spirocyclic oxindoles, α, β-unsaturated aldehydes
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-24590DOI: 10.1021/cs501975uISI: 000349275300086Scopus ID: 2-s2.0-84922713231OAI: oai:DiVA.org:miun-24590DiVA: diva2:795786
Available from: 2015-03-17 Created: 2015-03-17 Last updated: 2016-09-29Bibliographically approved

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Afewerki, SamsonMa, GuangningIbrahem, IsmailCordova, Armando
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