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Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid

We describe the asymmetric addition of unactivated α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid, generating an all-carbon quaternary stereocenter with broad substrate scope and high enantioselectivity. The products are easily transformed into their corresponding 1,5...

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Detalles Bibliográficos
Autores principales: Yang, Xiaoyu, Toste, F. Dean
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5155590/
https://www.ncbi.nlm.nih.gov/pubmed/27990248
http://dx.doi.org/10.1039/c5sc04202j
Descripción
Sumario:We describe the asymmetric addition of unactivated α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid, generating an all-carbon quaternary stereocenter with broad substrate scope and high enantioselectivity. The products are easily transformed into their corresponding 1,5- and 1,4-ketoaldehyde derivatives, which are both important building blocks in organic synthesis.