Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 26, Pages 7653-7656Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201502233
Keywords
asymmetric catalysis; carbonyl ylides; cycloaddition; rhodium; tropone
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Funding
- International Max Planck Research School in Chemical Biology
- FCI
- Deutsche Forschungsgemeinschaft (DFG) through the Cluster of Excellence RESOLV (Ruhr Explores Solvation) [EXC 1069]
- European Research Council under the Seventh Framework Programme of the European Union [268309]
- Max Planck Society
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We report a rhodium(II)-catalyzed highly enantioselective 1,3-dipolar cycloaddition reaction between the carbonyl moiety of tropone and carbonyl ylides to afford troponoids in good to high yields with excellent enantioselectivity. We demonstrate that -diazoketone-derived carbonyl ylides, in contrast to carbonyl ylides derived from diazodiketoesters, undergo [6+3] cycloaddition reactions with tropone to yield the corresponding bridged heterocycles with excellent stereoselectivity.
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