1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with a Cellulose-Derived Chiral Enone. A Novel Route for Organocatalysts Development

ARIEL M. SAROTTI; ROLANDO A. SPANEVELLO; ALEJANDRA G. SUÁREZ; GUSTAVO A. ECHEVERRÍA; OSCAR E. PIRO

ORGANIC LETTERS

AMER CHEMICAL SOC

Lugar: Washington; Año: 2012 vol. 14 p. 2556 - 2559

1523-7060

Cellulose-derived chiral pyrrolidines were synthesized in excellent yields, regio 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