IQUIR   05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone
Autor/es:
ZURITA, M. A.; AVILA, A.; SPANEVELLO, R.A.; SUÁREZ, A.G.; SAROTTI, A.M.*
Revista:
CARBOHYDRATE RESEARCH
Editorial:
ELSEVIER SCI LTD
Referencias:
Lugar: Amsterdam; Año: 2015 vol. 402 p. 67 - 70
ISSN:
0008-6215
Resumen:
A short and efficient methodology for the synthesis of chiral dioxa-caged Compounds from levoglucose-none, a biomass-derived enone, is herein Presented. The key transformation, that involves a cascade 3-step cationic cyclization, was efficiently carried out in high yields and selectivities by Montmorillonite K-10 catalysis. The usefulness of K-10 in related semi-pinacol rearrangements to obtain pyran-3-ones is also shown. Interesting differences in the reactivity pattern was found for epimeric alcohols, and the origins of these findings were determined by DFT calculations.