Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes
| Autor: | CDMF FAPESP, Rodrigo Bernárdez, Jesús A. Varela, Carlos Saa, Alvaro Velasco Rubio |
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| Přispěvatelé: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares, Universidade de Santiago de Compostela. Departamento de Química Orgánica |
| Rok vydání: | 2021 |
| Předmět: |
Metabolite
1 4-Benzodiazepine chemistry.chemical_element Pyrrolobenzodiazepine Hydroamination Catalysis Rhodium Benzodiazepines chemistry.chemical_compound Allenes Chemistry Organic Chemistry Enantioselective synthesis Stereoisomerism Note Lipids Combinatorial chemistry Hydrocarbons Lixivaptan Alkadienes Alkynes Mixtures 1 4-Benzoxazepine Layers |
| Zdroj: | Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela instname The Journal of Organic Chemistry |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.1c01268 |
| Popis: | 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® This work has received financial support from MINECO (project CTQ2017-87939R and ORFEO-CINQA network RED2018-102387-T), the Xunta de Galicia (project ED431C 2018/04 and Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/03) and the European Union (European Regional Development Fund – ERDF). A.V.-R. thanks Xunta de Galicia for a predoctoral fel-lowship (ED481A-2018/34, 2018-2021). SI |
| Databáze: | OpenAIRE |
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