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

Sarotti, Ariel Marcelo
Spanevello, Rolando Angel
Suarez, Alejandra Graciela
Echeverría, Gustavo Alberto
Piro, Oscar Enrique

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Publication date

May 2012

DOI

10.1021/ol3008588

Publisher

American Chemical Society (ACS)

ISSN

1523-7060

Journal

Organic Letters

Citation count (estimate)

Abstract

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.Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto...

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

Abstract

Extracted data

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

Abstract

Extracted data

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