1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with a Cellulose-Derived Chiral Enone. A Novel Route for Organocatalysts Development
Organic Letters2012Vol. 14(10), pp. 2556–2559
Citations Over TimeTop 11% of 2012 papers
Abstract
Cellulose-derived chiral pyrrolidines were synthesized in excellent yields, regioselectivities, and stereoselectivities via a 1,3-dipolar cycloaddition reaction between levoglucosenone and azomethine ylides. An unprecedented isomerization event led to a new family of pyrrolidines with an unusual relative stereochemistry. Preliminary results showed that these compounds are promising organocatalysts for iminium ion-based asymmetric Diels-Alder reactions.
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