info:eu-repo/semantics/article
1,3-Dipolar cycloaddition reactions of azomethine ylides with a cellulose-derived chiral enone. A novel route for organocatalysts development
Fecha
2012-05Registro en:
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
1523-7060
CONICET Digital
CONICET
Autor
Sarotti, Ariel Marcelo
Spanevello, Rolando Angel
Suarez, Alejandra Graciela
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
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.