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.
Quasienantiomeric Levoglucosenone and Isolevoglucosenone Allow the Parallel Kinetic Resolution of a Racemic Nitrone / F. CARDONA; D. LALLI; C. FAGGI; A. GOTI; A. BRANDI. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 73:(2008), pp. 1999-2002. [10.1021/jo702403b]
Quasienantiomeric Levoglucosenone and Isolevoglucosenone Allow the Parallel Kinetic Resolution of a Racemic Nitrone
CARDONA, FRANCESCA;FAGGI, CRISTINA;GOTI, ANDREA;BRANDI, ALBERTO
2008
Abstract
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.
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