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

SAROTTI, A.M.*; SPANEVELLO, R.A.; SUÁREZ, A.G.*; ECHEVERRÍA, G.A.; PIRO, O.E.

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, 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.-Alder reactions.