Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 45, Pages 13357-13361Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201505782
Keywords
benzazepines; cyclization; metallacyclopropenes; osmium catalysts; phenethylamines
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Funding
- MICINN [CTQ2011-28258, CTQ2014-52799-P, CTQ2014-51912REDC]
- Xunta de Galicia
- European Regional Development Fund [GRC2014/032, EM 2012/051]
- DGA [E-35]
- European Social Fund
- Spanish MICINN
- Juan de la Cierva Contract [JCI-2011-09946]
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A novel osmium-catalyzed cyclization of o-alkynyl phenethylamines to give 3-benzazepines is reported. The procedure allows the straightforward preparation of a broad range of dopaminergic 3-benzazepine derivatives. Mechanistic investigations revealed that the process takes place via osmacyclopropene intermediates, which were isolated and characterized by X-ray crystallography.
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