Journal
ORGANIC LETTERS
Volume 14, Issue 10, Pages 2556-2559Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol3008588
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- ANPCyT
- CONICET
- UNR from Argentina
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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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