Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone.

Mariano A Zurita, Aylén Avila, Rolando A Spanevello, Alejandra G Suárez, Ariel M Sarotti

Carbohydrate research 2015 Jan 30

filter terms:

A short and efficient methodology for the synthesis of chiral dioxa-caged compounds from levoglucosenone, 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. Copyright © 2014 Elsevier Ltd. All rights reserved.

Citation

Mariano A Zurita, Aylén Avila, Rolando A Spanevello, Alejandra G Suárez, Ariel M Sarotti. Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone. Carbohydrate research. 2015 Jan 30;402:67-70