A new Imidazole-Containing Imidazolidinone Catalyst for Organocatalyzed Asymmetric Conjugate Addition of Nitroalkanes to Aldehydes
2007 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, no 4-5, 740-748 p.Article in journal (Refereed) Published
Herein we report a new organocatalyst for the asymmetric Michael addition of nitroalkanes to α,β-unsaturated aldehydes. This catalyst incorporates a basic imidazole group in addition to the secondary amine responsible for activation of the α,β-unsaturated carbonyl compounds via iminium ion formation. The new organocatalyst is capable of catalyzing the enantioselective carbon-carbon bond formation with a high degree of enantiocontrol providing products in enantiomeric excesses of up to 92% and yields of up to to 91 %. These results constitute the best results so far reported for organocatalyzed Michael additions of nitroalkanes to α,β-unsaturated aldehydes, and provide proof of principle that organocatalysts incorporating two internal basic moieties may find broad application in organocatalyzed Michael additions.
Place, publisher, year, edition, pages
2007. Vol. 349, no 4-5, 740-748 p.
α, β-unsaturated aldehydes, Asymmetric catalysis, C-C coupling, Iminium ion activation, Michael addition, Organocatalysis
IdentifiersURN: urn:nbn:se:uu:diva-95939DOI: 10.1002/adsc.200600316ISI: 000245379400035OAI: oai:DiVA.org:uu-95939DiVA: diva2:170326