title: 1,3-Dipolar cycloaddition reactions of azomethine ylides with a cellulose-derived chiral enone. A novel route for organocatalysts development.
abstract: Cellulose-derived chiral pyrrolidines were synthesized in excellent yields, regioselectivities, and stereoselectivities via a 1,3-dipolar cycloaddition reaction between levoglucosenone and azomethine ylides. An unprecedented isomerization event led to a new family of pyrrolidines with an unusual relative stereochemistry. Preliminary results showed that these compounds are promising organocatalysts for iminium ion-based asymmetric Diels-Alder reactions.
authors.affiliation: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET , Suipacha 531, S2002LRK Rosario, Argentina, and Departamento de Física and Instituto IFLP (CONICET, CCT-La Plata), Facultad de Ciencias Exactas, Universidad Nacional de La Plata , 1900 La Plata, Argentina.
authors.forename: Ariel M
authors.initials: AM
authors.lastname: Sarotti
authors.forename: Rolando A
authors.initials: RA
authors.lastname: Spanevello
authors.forename: Alejandra G
authors.initials: AG
authors.lastname: Suárez
authors.forename: Gustavo A
authors.initials: GA
authors.lastname: Echeverría
authors.forename: Oscar E
authors.initials: OE
authors.lastname: Piro
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002384:Catalysis; D002482:Cellulose / Q000737:chemistry*; D061565:Cycloaddition Reaction; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007659:Ketones; D011759:Pyrrolidines; D013882:Thiosemicarbazones; C512188:azomethine; D002482:Cellulose; C512757:1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose; D005947:Glucose