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Achiral Co-Catalyst Induced Switches in Catalytic Asymmetric Reactions on Racemic Mixtures (RRM): From Stereodivergent RRM to Stereoconvergent Deracemization by Combination of Hydrogen Bond Donating and Chiral Amine Catalysts
Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden .
Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden .
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2012 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, no 14-15, 2865-2872 p.Article in journal (Refereed) Published
Abstract [en]

A stereochemical divergent approach for the highly enantioselective synthesis of distinct bicyclic products with multiple stereocenters from a racemate using a single chiral catalyst is disclosed. It is based on switches of the overall reaction pathways in the chiral amine-catalyzed cascade reactions between racemic ?-nitro ketones and a,beta-unsaturated aldehydes using different achiral co-catalysts. The utility of the method is exemplified by the highly diasteroselective switch and stereoconvergent deracemization process by combination of chiral amine and achiral hydrogen-bond-donating catalysts.

Place, publisher, year, edition, pages
2012. Vol. 354, no 14-15, 2865-2872 p.
Keyword [en]
cascade reactions; deracemization; dynamic asymmetric catalysis; hydrogen-bond donor; organocatalysis; reactions on racemic mixtures; stereodivergence
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-17532DOI: 10.1002/adsc.201200357ISI: 000309907300037Scopus ID: 2-s2.0-84869031085OAI: oai:DiVA.org:miun-17532DiVA: diva2:573457
Available from: 2012-11-30 Created: 2012-11-30 Last updated: 2012-12-13Bibliographically approved

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Ma, GuangningIbrahem, IsmailCordova, Armando
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