6533b834fe1ef96bd129e2d7
RESEARCH PRODUCT
Catalytic Diastereo- and Enantioselective Synthesis of 2-Imidazolinones.
Carlos VilaJosé R. PedroGonzalo BlayAmparo Sanz-marcoPablo Martínez-pardoAlba Escrivá-palomosubject
chemistry.chemical_classificationChemistryArylOrganic ChemistryEnantioselective synthesisBiochemistryCombinatorial chemistryCycloadditionCatalysisNitronechemistry.chemical_compoundCatàlisiLewis acids and basesPhysical and Theoretical ChemistryBifunctionalQuímica orgànicadescription
Chiral cyclic ureas (2-imidazolinones) were prepared by the reaction of nitrones and isocyanoacetate esters using a multicatalytic system that combines a bifunctional Brønsted base-squaramide organocatalyst and Ag+ as a Lewis acid. The reaction could be achieved with a range of nitrones derived from aryl- and cycloalkylaldehydes with moderate diastereo- and good enantioselectivity. A plausible mechanism involving an initial formal [3 + 3] cycloaddition of the nitrone and isocyanoacetate ester, followed by rearrangement to an aminoisocyanate and cyclization to the imidazolinone, is proposed.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2019-01-01 | Organic letters |