Enantioenriched alpha-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes
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| Title: | Enantioenriched alpha-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes |
| Author: | Velasco Rubio, Álvaro Bernárdez Alfaya, Rodrigo Varela Carrete, Jesús Ángel Saá Rodríguez, Carlos |
| Affiliation: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica |
| Subject: | Alkynes | Allenes | Rhodium | Hydroamination | 1,4-Benzodiazepine | 1,4-Benzoxazepine | |
| Date of Issue: | 2021 |
| Publisher: | American Chemical Society |
| Citation: | Velasco-Rubio, A., Bernárdez, R., Varela, J. A., Saá, C. (2021). Enantioenriched alpha-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes. J. Org. Chem. 86, 15, 10889-10902 |
| Abstract: | 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® |
| Description: | NOTICE: This is the peer reviewed version of the following article: Velasco-Rubio, A., Bernárdez, R., Varela, J. A., Saá, C. (2021). Enantioenriched alpha-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes. J. Org. Chem. 86, 15, 10889-10902. [doi: 10.1021/acs.joc.1c01268]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving |
| Publisher version: | https://doi.org/10.1021/acs.joc.1c01268 |
| Embargo: | 2022-07-15 |
| URI: | http://hdl.handle.net/10347/26925 |
| DOI: | 10.1021/acs.joc.1c01268 |
| ISSN: | 0022-3263 |
| E-ISSN: | 1520-6904 |
| Rights: | Copyright © 2021 American Chemical Society. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving |
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