TY - JOUR T1 - Imidazolidinone intermediates in prolinamide-catalyzed aldol reactions. AU - Fuentes de Arriba,Angel L, AU - Simón,Luis, AU - Raposo,César, AU - Alcázar,Victoria, AU - Sanz,Francisca, AU - Muñiz,Francisco M, AU - Morán,Joaquín R, Y1 - 2010/05/12/ PY - 2010/5/13/entrez PY - 2010/5/13/pubmed PY - 2010/5/13/medline SP - 2979 EP - 85 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 8 IS - 13 N2 - The reaction between acetone and 4-nitrobenzaldehyde catalyzed by aniline prolinamide 1 was studied in depth. Working in different solvents with equimolar amounts of reagents and monitoring the reaction by 1H NMR, we detected and identified several imidazolidinones, such as those of the acetone 4, the aldol products 5a and 5b, and aldehydes 10a and 10b. According to our results, these compounds could influence the reaction rate and diminish product enantioselectivity. Furthermore, acetone imidazolidinone 4 was seen to react with 4-nitrobenzaldehyde to furnish the aldol product 3. This reaction can be catalyzed by different nucleophiles and acids. In fact, strong acids such as camphorsulfonic or trifluoroacetic acid, convert imidazolidinones into iminium salts and afford more enantioselective aldol reactions when different aromatic prolinamides are used. Enantiomeric excesses of ca. 82% are reached. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/20461270/Imidazolidinone_intermediates_in_prolinamide_catalyzed_aldol_reactions_ L2 - https://doi.org/10.1039/b926284a DB - PRIME DP - Unbound Medicine ER -