Proline imidazolidinones and enamines in Hajos–Wiechert and Wieland–Miescher ketone synthesis

• Published in: Tetrahedron Vol. 65; no. 25; pp. 4841 - 4845
• Main Authors: de Arriba, Ángel L. Fuentes, Simón, Luis, Raposo, César, Alcázar, Victoria, Morán, Joaquín R.
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 20-06-2009; Elsevier
• Subjects: Catalysis; Catalysts: preparations and properties; Chemistry; Exact sciences and technology; General and physical chemistry; Hajos–Wiechert ketone; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Imidazolidinones and enamine intermediates; l-Prolinamide catalysis; Noncondensed benzenic compounds; Organic chemistry; Preparations and properties; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Wieland–Miescher ketone; Imidazolidinones and enamine intermediates; Hajos–Wiechert ketone; Wieland–Miescher ketone; l-Prolinamide catalysis; Intramolecular reaction; Imidazolidinones and enamine; Imidazole derivatives; Nitrogen heterocycle; Enamine; Hajos―Wiechert ketone; Proline; Aniline derivatives; intermediates; Aldol condensation; α-Aminoacid; Prolinamide catalysis; Aniline; Aminoacid; Acyl chloride; Benzenic compound; Enantiomeric excess; Aromatic compound; Catalysis; Chemical synthesis; Wieland―Miescher ketone; Catalyst
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2009.04.050

Readily available aromatic prolinamides obtained from the acid chloride of proline hydrochloride and anilines induce large enantiomeric excesses in intramolecular aldol condensations. Imidazolidinones derived from the reaction of the catalyst and enamines have been found as intermediates in these reactions.
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