Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 14, Pages 4600-4604Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201600654
Keywords
enantioselectivity; heterocycles; ring-opening reactions; rhodium; synthetic methods
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Funding
- National Sciences and Engineering Research Council (NSERC)
- Deutsche Forschungsgemeinschaft (DFG) [LO 2065/1-1]
- NSERC
- National Natural Science Foundation of China [21172148, 21202044]
- China Scholarship Council [201306745008]
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While the utility of vinylogous enolates is well established in the setting of vinylogous aldol, Mannich, and Michael chemistries, literature reports concerning -reactivity are scarce for other reaction classes. Presented herein is an unprecedented example of vinylogous reactivity exemplified by the rhodium-catalyzed asymmetric ring-opening reaction of oxabicycles. This strategy also provides a powerful route to incorporate the biologically useful coumarin motif into the hydronapthalene scaffold.
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