title: Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds derived from levoglucosenone.
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.
authors.affiliation: Instituto de Química de Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina.
authors.forename: Mariano A
authors.initials: MA
authors.lastname: Zurita
authors.affiliation: Instituto de Química de Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina.
authors.forename: Aylén
authors.initials: A
authors.lastname: Avila
authors.affiliation: Instituto de Química de Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina.
authors.forename: Rolando A
authors.initials: RA
authors.lastname: Spanevello
authors.affiliation: Instituto de Química de Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina.
authors.forename: Alejandra G
authors.initials: AG
authors.lastname: Suárez
authors.affiliation: Instituto de Química de Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina. Electronic address: sarotti@iquir-conicet.gov.ar.
authors.forename: Ariel M
authors.initials: AM
authors.lastname: Sarotti
mesh_terms: D001546:Bentonite / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; C503188:montmorillonite K-10; D001546:Bentonite; C512757:1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose; D005947:Glucose
keywords: Biomass; Caged compounds; Levoglucosenone; Montmorillonite K-10; Rearrangements