Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via enantioselective rhodium-catalyzed hydrofunctionalizations of alkynes and allenes

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URI: http://hdl.handle.net/10347/29033
ISSN: 0022-3263
DOI: 10.1021/acs.joc.1c01268

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2021

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ACS Publications
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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

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Allenes| Hydrocarbons| Layers| Lipids| Mixtures

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J. Org. Chem. 2021, 86, 10889−10902. https://doi.org/10.1021/acs.joc.1c01268

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This work received financial support from MINECO (project CTQ2017-87939-R 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 fellowship (ED481A-2018/34, 2018-2021)

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Attribution 4.0 International

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Química Orgánica