Pi-stacking effect on levoglucosenone derived internal chiral auxiliaries. A case of complete enantioselectivity inversion on the Diels-Alder reaction.
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.
Sarotti
Ariel M
AM
Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario - CONICET, Suipacha 531, S2002LRK Rosario, Argentina.
Fernández
Israel
I
Spanevello
Rolando A
RA
Sierra
Miguel A
MA
Suárez
Alejandra G
AG
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
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