Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 34, Pages 10074-10078Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201604937
Keywords
alkenes; heterocycles; isomerization; kinetic resolution; rhodium
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Funding
- National Sciences and Engineering Research Council (NSERC)
- Deutsche Forschungsgemeinschaft (DFG) [LO 2065/1-1]
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While desymmetrizations by intermolecular asymmetric ring-opening reactions of oxabicyclic alkenes with various nucleophiles have been reported over the past two decades, the demonstration of an intramolecular variant is unknown. Reported herein is the first rhodium-catalyzed asymmetric cycloisomerization of meso-oxabicyclic alkenes tethered to bridgehead nucleophiles, thus providing access to tricyclic scaffolds through a myriad of enantioselective C-O, C-N, and C-C bond formations. Moreover, we also demonstrate a unique parallel kinetic resolution, whereby racemic oxabicycles bearing two different bridgehead nucleophiles can be resolved enantioselectively.
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