Artículo

1,3-Dipolar cycloaddition reactions of azomethine ylides with a cellulose-derived chiral enone. A novel route for organocatalysts development

Sarotti, Ariel MarceloIcon ; Spanevello, Rolando AngelIcon ; Suarez, Alejandra GracielaIcon ; Echeverría, Gustavo AlbertoIcon ; Piro, Oscar EnriqueIcon
Fecha de publicación: 05/2012
Editorial: American Chemical Society
Revista: Organic Letters
ISSN: 1523-7060
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:

Resumen

Cellulose-derived chiral pyrrolidines were synthesized in excellent yields, regioselectivities, and stereoselectivities via a 1,3-dipolar cycloaddition reaction between levoglucosenone and azomethine ylides. An unprecedented isomerization event led to a new family of pyrrolidines with an unusual relative stereochemistry. Preliminary results showed that these compounds are promising organocatalysts for iminium ion-based asymmetric Diels-Alder reactions. © 2012 American Chemical Society.
Palabras clave: Organocatalyst , X-Ray Crystal Structure , Solution Nmr Structures
 
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info:eu-repo/semantics/openAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)
Identificadores
URI: http://hdl.handle.net/11336/76528
DOI: http://dx.doi.org/10.1021/ol3008588
Colecciones
Articulos(IFLP)
Articulos de INST.DE FISICA LA PLATA
Articulos(IQUIR)
Articulos de INST.DE QUIMICA ROSARIO
Citación
Sarotti, Ariel Marcelo; Spanevello, Rolando Angel; Suarez, Alejandra Graciela; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; 1,3-Dipolar cycloaddition reactions of azomethine ylides with a cellulose-derived chiral enone. A novel route for organocatalysts development; American Chemical Society; Organic Letters; 14; 10; 5-2012; 2556-2559
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