Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine

Construction of the hydroquinoline skeleton of symbioimine by Cu-mediated N-alkenylation or O-alkenylation of an allyl aminoalcohol, in which either chemoselectivity could lead to the target compound, was investigated. O-alkenylation followed by Claisen rearrangement was favored with high selectivit...

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Detalles Bibliográficos
Autores principales: Fujita, Rie, Hanaya, Kengo, Sugai, Takeshi, Higashibayashi, Shuhei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8674349/
https://www.ncbi.nlm.nih.gov/pubmed/34911981
http://dx.doi.org/10.1038/s41598-021-03448-9
Descripción
Sumario:Construction of the hydroquinoline skeleton of symbioimine by Cu-mediated N-alkenylation or O-alkenylation of an allyl aminoalcohol, in which either chemoselectivity could lead to the target compound, was investigated. O-alkenylation followed by Claisen rearrangement was favored with high selectivity under a ligand-free condition. Subsequent intramolecular condensation furnished the hydroquinoline skeleton of symbioimine.

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