Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 43, Pages 14250-14254Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809680
Keywords
asymmetric catalysis; atropisomers; C-H activation; heterocycles; rhodium
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Funding
- Max-Planck-Gesellschaft
- 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 (FP7/2007-2013)
- Max Planck Society
- European Research Council under the Seventh Framework Programme of the European Union (ERC) [268309]
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Axially chiral 4-arylisoquinolones are endowed with pronounced bioactivity, and methods for their efficient synthesis have gained widespread attention. However, enantioselective synthesis of axially chiral 4-arylisoquinolones by means of C-H activation has not been reported to date. Described here is a rhodium (III)-catalyzed C-H bond activation and annulation for the atroposelective synthesis of axially chiral 4-arylisoquinolones. The method employs chiral cyclopentadienyl ligands embodying a piperidine ring as backbone and yields the atropisomers with good to excellent yields and enantioselectivity. Biological relevance of the 4-arylisoquinolones was demonstrated by their investigation in different cellular assays, leading to the discovery of novel non-SMO (SMO = smoothened) binding Hedgehog pathway inhibitors.
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