Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 15, Pages 10889-10902Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01268
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Funding
- MINECO [CTQ2017-87939R]
- ORFEO-CINQA network [RED2018-102387-T]
- Xunta de Galicia [ED431C 2018/04, ED431G 2019/03, ED481A-2018/34]
- European Union (European Regional Development Fund, ERDF)
- (ERDF)
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Benzofused seven-membered heterocycles such as 1,4-BZDs and 1,4-BZOs were efficiently synthesized by Rh-catalyzed hydrofunctionalization of internal alkynes and allenes in good to excellent yields. Enantioselective hydroamination of (aminomethyl)anilines yielded 3-vinyl-1,4-BZDs with excellent enantioselectivities, and orthogonal N-deprotection of 1,4-BZDs allowed for the easy entry to an advanced pyrrolobenzodiazepine metabolite of the V2-receptor antagonist Lixivaptan.
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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