Enantioselective Addition of Alkynyl Ketones to Nitroolefins Assisted by Bronsted Base/H-Bonding Catalysis

Various sets of enolizable alkynyl ketones (including methyl ynones with α-aryl, α-alkenyl, and α-alkoxy groups) were able to react smoothly with nitroolefins with the assistance of bifunctional Brønsted base/H-bond catalysts to provide adducts with two consecutive tertiary stereocenters in a highly...

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Detalles Bibliográficos
Autores: Campano García, Teresa Esperanza, Iriarte Arrieta, Igor, Olaizola Aizpuru, Olatz, Etxabe Tellería, Julen, Mielgo Vicente, María Antonia, Gamboa Landa, José Ignacio, Odriozola, José M., García, Jesús María, 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:10810/65179
Acceso en línea:http://hdl.handle.net/10810/65179
Access Level:acceso abierto
Palabra clave:alkynyl ketones
asymmetric catalysis
Brønsted bases
Michael reaction
organocatalysis
Descripción
Sumario:Various sets of enolizable alkynyl ketones (including methyl ynones with α-aryl, α-alkenyl, and α-alkoxy groups) were able to react smoothly with nitroolefins with the assistance of bifunctional Brønsted base/H-bond catalysts to provide adducts with two consecutive tertiary stereocenters in a highly diastereo- and enantioselective fashion. Further transformation of the obtained adducts into optically active acyclic and polycyclic molecules, including some with intricate carbon skeletons, was also demonstrated.

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