Quasienantiomeric levoglucosenone and isolevoglucosenone allow the parallel kinetic resolution of a racemic nitrone.
Cycloadditions of chiral pyrroline N-oxides to levoglucosenone (1) and isolevoglucosenone (2) proceed with a high level of double asymmetric induction. Partial kinetic resolutions (KR) of both enantiomers of a racemic nitrone 3 were achieved, and a parallel kinetic resolution (PKR) experiment allowed the stereoselective divergent synthesis of two quasienantiomeric imino-C-disaccharide precursors.
Cardona
Francesca
F
Department of Organic Chemistry U. Schiff, Polo Scientifico e Tecnologico, University of Florence, Italy, Via della Lastruccia 13, I-50019 Sesto Fiorentino, Italy. francesca.cardona@unifi.it
Lalli
Daniela
D
Faggi
Cristina
C
Goti
Andrea
A
Brandi
Alberto
A
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry; D007700:Kinetics; D009589:Nitrogen Oxides / Q000737:chemistry*; D013237:Stereoisomerism
C476164:1,6-anhydro-2,3-dideoxyhex-3-enopyran-4-ulose; D019086:Bridged Bicyclo Compounds, Heterocyclic; D009589:Nitrogen Oxides; C015388:nitrones; C512757:1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose; D005947:Glucose