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Towards an asymmetric organocatalytic α-cyanation of β-ketoesters

This communication describes the first proof of concept for an asymmetric α-cyanation of β-ketoesters using a hypervalent iodine-based electrophilic cyanide-transfer reagent. A series of different organocatalysts has been investigated and it was found that the use of naturally occurring Cinchona alk...

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Detalles Bibliográficos
Autores principales: Chowdhury, Raghunath, Schörgenhumer, Johannes, Novacek, Johanna, Waser, Mario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4366011/
https://www.ncbi.nlm.nih.gov/pubmed/25843983
http://dx.doi.org/10.1016/j.tetlet.2015.02.116
Descripción
Sumario:This communication describes the first proof of concept for an asymmetric α-cyanation of β-ketoesters using a hypervalent iodine-based electrophilic cyanide-transfer reagent. A series of different organocatalysts has been investigated and it was found that the use of naturally occurring Cinchona alkaloids allows obtaining the target products in good yields and with moderate enantioselectivities up to er = 76:24 under operationally simple conditions.