INVESTIGADORES
PIRO Oscar Enrique
artículos
Título:
1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with a Biomass-Derived Chiral Enone. A Novel Route for Organocatalysts Development
Autor/es:
A. M. SAROTTI; R. A. SPANEVELLO; A. G. SUÁREZ; G. A. ECHEVERRÍA; O. E. PIRO
Revista:
ORGANIC LETTERS
Editorial:
AMER CHEMICAL SOC
Referencias:
Lugar: Washington; Año: 2012 vol. 14 p. 2556 - 2559
ISSN:
1523-7060
Resumen:
A conceptually novel route for organocatalyst development is described. Biomass-derived chiral pyrrolidines were synthesized in excellent yields, regio and stereoselectivities via 1,3-dipolar cycloaddition reaction between levoglucosenone and azomethine ylides. An unprecedented isomerization led to a new family of pyrrolidines with an unusual relative stereochemistry. Preliminary results showed that these compounds are efficient and highly promising organocatalysts for iminium ion-based asymmetric Diels-Alder reactions.
