RESUMO
A series of thiourea-amine bifunctional catalysts have been developed by a rational combination of prolines with cinchona alkaloids, which are connected by a thiourea motif. The catalyst 3a, prepared from L-proline and cinchonidine, was found to be a highly efficient catalyst for the conjugate addition of ketones/aldehydes to a wide range of nitroalkenes (up to 98/2 dr and 96% ee). The privileged cinchonidine backbone and the thiourea motif are essential to the reaction activity and enantioselectivity.
Assuntos
Aldeídos/química , Alcenos/química , Aminas/química , Reagentes de Ligações Cruzadas/química , Cetonas/química , Tioureia/química , Catálise , Alcaloides de Cinchona/química , Prolina/químicaRESUMO
A Brønsted acid catalyzed tandem Diels-Alder/aromatization reaction of 2-vinylindoles has been developed. The reaction provides a highly efficient and concise approach to 3-indolyl-substituted tetrahydrocarbazoles with various substituents in high yields under mild conditions.
Assuntos
Indóis/química , Ácido Trifluoracético/química , Carbazóis/química , CatáliseRESUMO
A novel cascade organocatalysis that allows efficient and rapid access to diverse and structurally complex oxazolidin-2-ones from simple starting materials and catalysts has been developed. A possible mechanism of this reaction has been proposed based on D- and 13C-labeling experiments.
Assuntos
Alcenos/química , Oxazolidinonas/síntese química , Piridinas/química , Compostos de Enxofre/química , Tioureia/química , Catálise , Nitrocompostos/químicaRESUMO
An enantioselective organocatalytic intramolecular ring-closing Friedel-Crafts-type alkylation of indolyl alpha,beta-unsaturated aldehydes has been developed. This powerful new strategy allows enantioselective access to THPIs and THBCs in a straightforward and atom-economical manner.
Assuntos
Indóis/química , Aldeídos/química , Alquilação , Catálise , Cristalografia por Raios X , Ciclização , Indóis/síntese química , Modelos Moleculares , Estrutura Molecular , EstereoisomerismoRESUMO
A hydrogen bonding-mediated double Michael addition-aromatization cascade of 2-propenylindoles and nitroolefins has been disclosed. The methodology allows an efficient synthesis of diverse and structurally complex tetrahydrocarbazoles in good to excellent enantioselectivities and diastereoselectivities.