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Highly Enantioselective Control of Dynamic Cascade Transformations by Dual Catalysis: Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). Mid-Sweden University, Sweden.
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
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2015 (English)In: ACS Catalysis, ISSN 2155-5435, E-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]
asymmetric cocatalysis, alpha, beta-unsaturated aldehydes, dynamic transformations, polysubstituted, spirocyclic oxindoles, all-carbon quaternary stereocenter
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-115699DOI: 10.1021/cs501975uISI: 000349275300086OAI: oai:DiVA.org:su-115699DiVA: diva2:799176
Note

AuthorCount:6;

Available from: 2015-03-30 Created: 2015-03-27 Last updated: 2017-12-04Bibliographically approved

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