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Highly Enantioselective Control of Dynamic Cascade Transformations by Dual Catalysis: Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles
Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Avdelningen för naturvetenskap. Stockholm Univ, Berzelii Ctr EXSELENT, SE-10691 Stockholm, Sweden.ORCID-id: 0000-0002-5108-6487
Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Avdelningen för naturvetenskap.
Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Avdelningen för kemiteknik.
Department of Materials and Environmental Chemistry, Stockholm University, Stockholm, Sweden .
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2015 (engelsk)Inngår i: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 5, nr 2, s. 1266-1272Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2015. Vol. 5, nr 2, s. 1266-1272
Emneord [en]
all-carbon quaternary stereocenter, asymmetric cocatalysis, dynamic transformations, polysubstituted, spirocyclic oxindoles, α, β-unsaturated aldehydes
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Identifikatorer
URN: urn:nbn:se:miun:diva-24590DOI: 10.1021/cs501975uISI: 000349275300086Scopus ID: 2-s2.0-84922713231OAI: oai:DiVA.org:miun-24590DiVA, id: diva2:795786
Tilgjengelig fra: 2015-03-17 Laget: 2015-03-17 Sist oppdatert: 2017-12-04bibliografisk kontrollert

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