title: Pi-stacking effect on levoglucosenone derived internal chiral auxiliaries. A case of complete enantioselectivity inversion on the Diels-Alder reaction.
abstract: Detailed quantum chemical calculations, experimental evidence, and NMR data rationalize the participation of pi-stacking interaction in the highly asymmetric Diels-Alder reaction using levoglucosenone derived internal chiral auxiliaries, including the appealing effect of inversion of the enantioselectivity by coordination of the substrate with Et 2AlCl.
authors.affiliation: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario - CONICET, Suipacha 531, S2002LRK Rosario, Argentina.
authors.forename: Ariel M
authors.initials: AM
authors.lastname: Sarotti
authors.forename: Israel
authors.initials: I
authors.lastname: Fernández
authors.forename: Rolando A
authors.initials: RA
authors.lastname: Spanevello
authors.forename: Miguel A
authors.initials: MA
authors.lastname: Sierra
authors.forename: Alejandra G
authors.initials: AG
authors.lastname: Suárez
mesh_terms: D000535:Aluminum / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D003517:Cyclopentanes; D004952:Esters; D009942:Organometallic Compounds; C512757:1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose; D000535:Aluminum; D005947:Glucose