Asymmetric assembly of all‐carbon tertiary/quaternary nonadjacent stereocenters through organocatalytic conjugate addition of α‐cyanoacetates to a methacrylate equivalent

An efficient, highly diastereo- and enantioselective assembly of acyclic carbonyl fragments possessing nonadjacent all-carbon tertiary/quaternary stereoarrays is reported based on a Brønsted base catalyzed Michael addition/a-protonation sequence involving a-cyanoacetates and 2,4-dimethyl-4-hydroxype...

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Detalles Bibliográficos
Autores: Iriarte, Igor, Vera, Silvia, Badiola, Eider, Mielgo, Antonia, Oiarbide, Mikel, García Castillo, Jesús María, Odriozola Ibarguren, José Manuel, Palomo, Claudio
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
País:España
Institución:Universidad Pública de Navarra
Repositorio:Academica-e. Repositorio Institucional de la Universidad Pública de Navarra
OAI Identifier:oai:academica-e.unavarra.es:2454/47251
Acceso en línea:https://hdl.handle.net/2454/47251
Access Level:acceso abierto
Palabra clave:Asymmetric organocatalysis
Michael reactions
Stereoselective protonation
Quaternary stereocenters
Brønsted bases
Descripción
Sumario:An efficient, highly diastereo- and enantioselective assembly of acyclic carbonyl fragments possessing nonadjacent all-carbon tertiary/quaternary stereoarrays is reported based on a Brønsted base catalyzed Michael addition/a-protonation sequence involving a-cyanoacetates and 2,4-dimethyl-4-hydroxypenten-3-one as novel methacrylate equivalent.