2-Aminoimidazolyl and 2-Aminopyridyl (S)-Prolinamides as Versatile Multifunctional Organic Catalysts for Aldol, Michael, and Diels–Alder Reactions
Articolo
Data di Pubblicazione:
2013
Citazione:
2-Aminoimidazolyl and 2-Aminopyridyl (S)-Prolinamides as Versatile
Multifunctional Organic Catalysts for Aldol, Michael, and Diels–Alder
Reactions / M. Orlandi, M. Benaglia, L. Raimondi, G. Celentano. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 12(2013), pp. 2346-2354. [10.1002/ejoc.201201643]
Abstract:
The synthesis of multifunctional organocatalysts, easily obtained
by the condensation of (S)-proline with 2-aminopyridine, 2,6-diaminopyridine, or 2-aminoimidazole, is reported.
These chiral prolinamides promoted the aldol condensation between cyclohexanone and different aromatic aldehydes with moderate to very high enantioselectivities (up to 98%
ee), depending on the nature of the substituents on the aryl
ring. Computational studies were performed to clarify the
stereochemical behaviour of the two different types of catalysts
and to understand the role of the different structural components of the chiral prolinamides in the recognition processes between the catalysts and the reactants. In preliminary experiments, trifluoroacetate salts of the chiral prolinamides have been used for the first time as catalysts in Diels–
Alder reactions between cyclopentadiene and cinnamaldehyde and in Michael reactions.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Aldol reactions; Enantioselectivity; Organocatalysis; Prolinamides
Elenco autori:
M. Orlandi, M. Benaglia, L. Raimondi, G. Celentano
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