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Quasienantiomeric Levoglucosenone and Isolevoglucosenone Allow the Parallel Kinetic Resolution of a Racemic Nitrone

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posted on 07.03.2008, 00:00 authored by Francesca Cardona, Daniela Lalli, Cristina Faggi, Andrea Goti, Alberto Brandi
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.