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- Title
Rhodium-Catalyzed Asymmetric Cycloisomerization and Parallel Kinetic Resolution of Racemic Oxabicycles.
- Authors
Loh, Charles C. J.; Schmid, Matthias; Webster, Robert; Yen, Andy; Yazdi, Shabnam K.; Franke, Patrick T.; Lautens, Mark
- Abstract
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.
- Subjects
RHODIUM catalysts; CYCLOISOMERIZATION; TISSUE scaffolds; NUCLEOPHILES; ALKENES
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 34, p10074
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201604937