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
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
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.
cascade reactions, deracemization, dynamic asymmetric catalysis, hydrogen-bond donor, organocatalysis, reactions on racemic mixtures, stereodivergence
IdentifiersURN: urn:nbn:se:su:diva-82964DOI: 10.1002/adsc.201200357ISI: 000309907300037OAI: oai:DiVA.org:su-82964DiVA: diva2:576851
FunderSwedish Research Council