Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes

[Image: see text] 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 (...

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Autores principales: Velasco-Rubio, Álvaro, Bernárdez, Rodrigo, Varela, Jesús A., Saá, Carlos
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8499028/
https://www.ncbi.nlm.nih.gov/pubmed/34259003
http://dx.doi.org/10.1021/acs.joc.1c01268
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author Velasco-Rubio, Álvaro
Bernárdez, Rodrigo
Varela, Jesús A.
Saá, Carlos
author_facet Velasco-Rubio, Álvaro
Bernárdez, Rodrigo
Varela, Jesús A.
Saá, Carlos
author_sort Velasco-Rubio, Álvaro
collection PubMed
description [Image: see text] 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 V(2)-receptor antagonist Lixivaptan.
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spelling pubmed-84990282021-10-12 Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes Velasco-Rubio, Álvaro Bernárdez, Rodrigo Varela, Jesús A. Saá, Carlos J Org Chem [Image: see text] 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 V(2)-receptor antagonist Lixivaptan. American Chemical Society 2021-07-14 2021-08-06 /pmc/articles/PMC8499028/ /pubmed/34259003 http://dx.doi.org/10.1021/acs.joc.1c01268 Text en © 2021 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Velasco-Rubio, Álvaro
Bernárdez, Rodrigo
Varela, Jesús A.
Saá, Carlos
Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes
title Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes
title_full Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes
title_fullStr Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes
title_full_unstemmed Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes
title_short Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes
title_sort enantioenriched α-vinyl 1,4-benzodiazepines and 1,4-benzoxazepines via enantioselective rhodium-catalyzed hydrofunctionalizations of alkynes and allenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8499028/
https://www.ncbi.nlm.nih.gov/pubmed/34259003
http://dx.doi.org/10.1021/acs.joc.1c01268
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