Search results for "Imidazolidinone"
showing 3 items of 3 documents
Inhibition of imidazolidinone intermediate formation in the aldol reactions catalyzed by zinc–prolinamide complexes
2011
Abstract The use of zinc salts as cocatalysts in aldol condensations catalyzed by single prolinamide (and in the extension by other more complex prolinamides) can prevent the formation of the parasitic intermediate imidazolidinone, with faster and also more stereoselective reactions than those catalyzed by the free amine. This new finding, together with this ion’s already known properties, make zinc salts highly suitable additives for aldol reactions catalyzed for prolinamide derivatives.
Recyclable Heterogeneous and Low-Loading Homogeneous Chiral Imidazolidinone Catalysts for α-Alkylation of Aldehydes
2014
Two polystyrene-supported and six homogeneous MacMillan imidazolidinone catalysts were prepared and tested for the asymmetric α-alkylation of propanal with benzodithiolylium tetrafluoroborate. The chiral imidazolidinone was linked to polystyrene through the N-3 atom or through the phenyl ring and their catalytic activity was compared with that of their unsupported precursors. This comparison has allowed us to find an unsupported catalyst that displays high catalytic activity down to 5 or 2 mol % at room temperature with a high level of enantioselectivity also when used with hexanal and 3-phenylpropanal. In addition, one of the heterogeneous materials was revealed to be highly recyclable for…
Transamidation reactions of 2-(2-sulfonylguanidino)acetamides
2007
Abstract The reactivity of a series of sulfonylguanidinoacetamides 2A–E towards amines is reported. Guanidinoacetamides 2A–C, containing the arylsulfonylimino moiety, undergo a facile transamidation to give substituted carboxamides 4A–C, through the imidazolidinone intermediate 3. Acetamide 2D, having a methanesulfonylimino substituent, affords the imidazolidinone 3D and no transamidated carboxamides 4 are detected. In the case of guanidinoacetamide 2E, with a p-nitrobenzenesulfonylimino substituent, a Smiles rearrangement was observed.