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

Carbohydr Res. 2015 Jan 30:402:67-70. doi: 10.1016/j.carres.2014.07.019. Epub 2014 Aug 1.

Abstract

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.

Keywords: Biomass; Caged compounds; Levoglucosenone; Montmorillonite K-10; Rearrangements.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bentonite / chemistry*
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Carbohydrate Conformation
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Glucose / analogs & derivatives*
  • Glucose / chemical synthesis
  • Glucose / chemistry
  • Models, Molecular
  • Stereoisomerism

Substances

  • Bridged Bicyclo Compounds, Heterocyclic
  • montmorillonite K-10
  • Bentonite
  • 1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose
  • Glucose