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 CatalystsShow others and affiliations
2012 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, no 14-15, p. 2865-2872Article 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, p. 2865-2872
Keywords [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, id: diva2:573457
2012-11-302012-11-302025-09-25Bibliographically approved