Repositorio UFRO · Omeka S

Computational Comparison of the Stability of Iminium Ions and Salts from Enals and Pyrrolidine Derivatives (Aminocatalysts)

Primer Autor	Costa, Anna M.
Co-autores	Castro-Alvarez, Alejandro Fillot, Daniel Vilarrasa, Jaume
Título	Computational Comparison of the Stability of Iminium Ions and Salts from Enals and Pyrrolidine Derivatives (Aminocatalysts)
Editorial	WILEY-V C H VERLAG GMBH
Revista	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Lenguaje	en
Resumen	The energies of CH2=CH-CH=N+R2 + HNR(2)-> CH2=CH-CH=N+R(2) + HNR2 reactions (exchange of propenal between two secondary amines) and of similar equilibria with cinnamaldehyde have been calculated and compared. Iminium ions from pyrrolidines with substituents that can help stabilize the positive charge are especially stable in the gas phase, as expected, whereas in very polar solvents the predicted order of stability (of their iminium ions) is: O-tert-butyldiphenylsilylprolinol > pyrrolidine > O-methylprolinol > 2-tert-butylpyrrolidine > Jorgensen-Hayashi catalyst > 2-tritylpyrrolidine > N,N-dimethylprolinamide > trimethylsilyl prolinate > 3-triflamidopyrrolidine>methyl prolinate >> MacMillan-1 catalyst > MacMillan-2 catalyst. When ion pairs such as iminium tetrafluoroborates, in CHCl3, are compared, the order is similar. These data can be used to predict which iminium salts may predominate when two or more secondary amines and appropriate acids are added to conjugated carbonyl compounds.
Tipo de Recurso	artículo original
doi	10.1002/ejoc.202200627
Formato Recurso	PDF
Palabras Claves	Asymmetric Michael reactions Chiral iminium ions Iminium tetrafluoroborates Organocatalysis Theoretical chemistry RELATIVE STABILITY SILYL ETHERS ORGANOCATALYSIS MECHANISM DIARYLPROLINOL REACTIVITY ALDEHYDES AMINE IMIDAZOLIDINONES REGENERATION
Ubicación del archivo	http://dx.doi.org/10.1002/ejoc.202200627
Categoría OCDE	Química Orgánica
Materias	Reacciones asimétricas de Michael Iones de iminio quirales Tetrafluoroboratos de iminio Organocatálisis Química teórica ESTABILIDAD RELATIVA ÉTERES SILÍLICOS ORGANOCATÁLISIS MECANISMO DIARILPROLINOL REACTIVIDAD ALDEHÍDOS AMINA IMIDAZOLIDINONAS REGENERACIÓN
Disciplinas de la OCDE	Química Orgánica Físico-Química Otras Especialidades de la Química
Versión del recurso (Recomendado-único)	version publicada
Tipo de ruta	hibrida verde
Access Rights	acceso abierto
Derechos de acceso	acceso abierto
Id de Web of Science	WOS:000854557800001
Título de la cita (Recomendado-único)	Computational Comparison of the Stability of Iminium Ions and Salts from Enals and Pyrrolidine Derivatives (Aminocatalysts)
Identificador del recurso (Mandatado-único)	artículo original
License	CC BY-NC 4.0
Condición de la licencia (Recomendado-repetible)	CC BY-NC 4.0