Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via enantioselective rhodium-catalyzed hydrofunctionalizations of alkynes and allenes
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Título: | Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via enantioselective rhodium-catalyzed hydrofunctionalizations of alkynes and allenes |
Autor/a: | Velasco Rubio, Álvaro Bernárdez Alfaya, Rodrigo Varela Carrete, Jesús Ángel Saá Rodríguez, Carlos |
Centro/Departamento: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica |
Palabras chave: | Allenes | Hydrocarbons | Layers | Lipids | Mixtures | |
Data: | 2021 |
Editor: | ACS Publications |
Cita bibliográfica: | J. Org. Chem. 2021, 86, 10889−10902. https://doi.org/10.1021/acs.joc.1c01268 |
Resumo: | Benzofused seven-membered heterocycles such as 1,4-benzo[e]diazepines (1,4-BZDs) and 1,4-benzo[e]oxazepines (1,4-BZOs) were efficiently synthesized by Rh-catalyzed hydrofunctionalization of internal alkynes and allenes in good to excellent yields. The asymmetric hydroamination of (aminomethyl)anilines gave rise to 3-vinyl-1,4-BZDs with excellent enantioselectivities. Orthogonal N-deprotection of 1,4-BZDs allowed an easy entry to an advanced pyrrolobenzodiazepine metabolite of the V2-receptor antagonist Lixivaptan |
Versión do editor: | https://doi.org/10.1021/acs.joc.1c01268 |
URI: | http://hdl.handle.net/10347/29033 |
DOI: | 10.1021/acs.joc.1c01268 |
ISSN: | 0022-3263 |
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