Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides

Stereoselective synthesis of pyrazolidinones via dipolar cycloaddition of azomethine imines with active esters under Lewis base catalysis is presented. The active esters are readily generated in situ from the corresponding acids. Products, which are obtained with excellent diastereocontrol and high...

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Detalles Bibliográficos
Autores principales: Hesping, Lena, Biswas, Anup, Daniliuc, Constantin G., Mück-Lichtenfeld, Christian, Studer, Armido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5811128/
https://www.ncbi.nlm.nih.gov/pubmed/29541440
http://dx.doi.org/10.1039/c4sc02612h
Descripción
Sumario:Stereoselective synthesis of pyrazolidinones via dipolar cycloaddition of azomethine imines with active esters under Lewis base catalysis is presented. The active esters are readily generated in situ from the corresponding acids. Products, which are obtained with excellent diastereocontrol and high enantioselectivity, contain along with the pyrazolidinone core also the tetrahydroisoquinoline structural motif. Theoretical studies give insight into the mechanism of the formal cycloaddition reaction.

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