Brønsted Base Catalyzed One-Pot Synthesis od Stereodefined Six-Member Carbocycles Featuring Transient Trienolates and a Key Intramolecular 1,6-Addition

Acatalyst-driven one-pot reaction sequence is developed for the enantio- and diastereoselective synthesis of tetrasubstituted cyclohexenes from simple unsaturated ketones or thioesters.The method involves atertiary amine/squara- mide-catalyzed a-selective addition of transiently generated trienolate...

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Detalles Bibliográficos
Autores: Olaizola Aizpuru, Olatz, Iriarte Arrieta, Igor, Zanella, Giovanna, Gómez Bengoa, Enrique, Gamboa Landa, José Ignacio, Oyarbide Garmendia, Juan Miguel, Palomo Nicolau, Claudio
Tipo de recurso: artículo
Fecha de publicación:2019
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/52087
Acceso en línea:http://hdl.handle.net/10810/52087
Access Level:acceso abierto
Descripción
Sumario:Acatalyst-driven one-pot reaction sequence is developed for the enantio- and diastereoselective synthesis of tetrasubstituted cyclohexenes from simple unsaturated ketones or thioesters.The method involves atertiary amine/squara- mide-catalyzed a-selective addition of transiently generated trienolates to nitroolefins,subsequent base-catalyzed double bond isomerization, and an intramolecular (vinylogous) 1,6- addition reaction, arare key carbocyclization step that proceeded with essentially perfect stereocontrol

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