Search results for "Aza-Michael"
showing 10 items of 10 documents
Asymmetric synthesis of 3,3′-pyrrolidinyl-dispirooxindoles via a one-pot organocatalytic Mannich/deprotection/aza-Michael sequence
2016
Chemical communications 52, 2249-2252 (2016). doi:10.1039/C5CC10057G
Straightforward One-Pot Synthesis of New 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Derivatives: X-ray Single Crystal Structure and Hirshfeld Ana…
2022
A straightforward one-pot route for the synthesis of a new 4-phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one is reported form the direct hydrazinolysis of triketo ester and hydrazine hydrate in ethanol. 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one was subjected to aza-Michael addition and N-alkylation on reaction with a set of alkylating agents in the presence of K2CO3. Hydrazinolysis of 4-phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one ester to hydrazide and conversion of hydrazide to thiosemicarbazide were successful. X-Ray single crystals analysis and 1H, 13C NMR were used for unambiguous structure confirmation. The O…H, N…H, C…N and C…C in 2, and the N…H, …
Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide
2011
The organocatalytic synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide is described. It involved, as the key step, an enantioselective intramolecular aza-Michael reaction (IMAMR) catalyzed by Jorgensen catalyst I, affording the common precursor with high enantioselectivity. This compound was subsequently transformed into the three alkaloids in a highly diastereoselective manner. (C) 2011 Elsevier Ltd. All rights reserved.
Nuevas aplicaciones de la reacción aza-Michael intramolecular asimétrica
2018
La reacción aza-Michael está considerada como una de las metodologías más atractivas para la preparación de derivados -amino carbonílicos. Así, la adición conjugada de una fuente de nitrógeno nucleófila a un sistema -insaturado es un camino eficiente para generar enlaces C-N. Esta reacción adquiere una especial relevancia en su versión intramolecular, ya que conduce a la formación de heterociclos nitrogenados de manera directa. Además, cuando la olefina activada contiene centros proquirales, se generan uno o varios estereocentros en el proceso. Por tanto, la versión asimétrica de esta transformación nos conducirá a la síntesis de heterociclos nitrogenados funcionalizados de forma estere…
N-sulfinyl amines as a nitrogen source in the asymmetric intramolecular aza-Michael reaction: total synthesis of (-)-pinidinol.
2010
N-Sulfinyl amines have been successfully employed as nitrogen nucleophiles for the asymmetric intramolecular aza-Michael reaction. The synthetic strategy involves a cross-metathesis reaction followed by the Michael-type cyclization, either in a base-catalyzed two-step procedure or in a tandem fashion. The developed methodology allows access to chiral substituted pyrrolidines and piperidines bearing one or two stereocenters and it has been applied to the synthesis of the piperidine alkaloid (-)-pinidinol.
A new strategy for the synthesis of fluorinated 3,4-dihydropyrimidinones
2009
A new family of 3,4-dihydropyrimidinones (DHPMs) bearing fluorinated substituents at C6 have been prepared from gem-difluorinated nitriles, alkyl 3-butenoates and iso(thio)cyanates. This novel Biginelli-type process relies on the gamma-addition of the ester-derived enolate to fluorinated nitriles. A tandem nucleophilic addition aza-Michael reaction sequence completes the synthetic process. (C) 2009 Elsevier B.V. All rights reserved.
Organocatalytic enantioselective synthesis of trifluoromethyl-containing tetralin derivatives by sequential (hetero)Michael reaction–intramolecular n…
2017
The enantioselective synthesis of tetralin derivatives bearing a trifluoromethylated all‐carbon quaternary stereocenter has been accomplished through a synthetic sequence comprising an organocatalytic β‐functionalization of ortho‐1‐trifluoromethylvinyl‐(hetero)aromatic conjugated aldehydes followed by the intramolecular nitrone 1,3‐cycloaddition reaction (INCR). Both nitromethane and N‐Cbz‐hydroxylamine were employed as nucleophiles in the initial organocatalytic conjugate addition step, which provided the chiral information required for the subsequent diastereoselective INCR. Although diastereoselectivity was moderate, good yields and enantioselectivities were, in general, obtained. Intere…
Base-Dependent Stereodivergent Intramolecular Aza-Michael Reaction: Asymmetric Synthesis of 1,3-Disubstituted Isoindolines
2013
The nucleophilic addition (A(N)) / intramolecular aza-Michael reaction (IMAMR) process on Ellman's tert-butylsulfinyl imines, bearing a Michael acceptor in the ortho position, is studied. This reaction affords 1,3-disubstituted isoindolines with a wide range of substituents in good yields and diastereoselectivities. Interestingly, careful choice of the base for the aza-Michael step allows either the cis or the trans diastereoisomers to be exclusively obtained. This stereodivergent cyclization has enabled the synthesis of C2-symmetric bisacetate-substituted isoindolines. In addition, bisacetate isoindolines bearing two well-differentiated ester moieties are also noteworthy because they may a…
Organocatalytic approach to benzofused nitrogen-containing heterocycles: enantioselective total synthesis of (+)-angustureine.
2008
Nuevas metodologías en la reacción aza-Michael intramolecular organocatalítica
2022
La síntesis asimétrica es un área clave en la Química moderna, especialmente relevante en la industria farmacéutica dada la íntima relación entre la actividad biológica de las biomoléculas y su estereoquímica. Al mismo tiempo, la concienciación sobre la contaminación y los múltiples problemas que esta puede ocasionar, ha impulsado que estas metodologías sean más ecológicas y respetuosas con en el medio ambiente. En este sentido, la organocatálisis se ha revelado en los últimos años como una de las estrategias más interesantes para la obtención de compuestos enantioenriquecidos. En consecuencia, nuestro grupo de investigación se ha centrado en la aplicación de dicha estrategia a la reacción …