Asymmetric assembly of all‐carbon tertiary/quaternary nonadjacent stereocenters through organocatalytic conjugate addition of α‐cyanoacetates to a methacrylate equivalent
Fecha
2016Autor
Versión
Acceso abierto / Sarbide irekia
Tipo
Artículo / Artikulua
Versión
Versión aceptada / Onetsi den bertsioa
Impacto
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10.1002/chem.201603082
Resumen
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. ...
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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. [--]
Materias
Asymmetric organocatalysis,
Michael reactions,
Stereoselective protonation,
Quaternary stereocenters,
Brønsted bases
Editor
Wiley
Publicado en
Chemistry – A European Journal 2016, 22, 13690 – 13696
Departamento
Universidad Pública de Navarra. Departamento de Química Aplicada /
Nafarroako Unibertsitate Publikoa. Kimika Aplikatua Saila
Versión del editor
Entidades Financiadoras
Support was provided by the University of the Basque Country UPV/EHU (UFI 11/22), Gobierno Vasco (GV,GrantNoIT-628-13),and Ministerio de Economía y Competitividad (MEC,Grant CTQ 2013-47925-C2), Spain.