Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 20, Pages 5895-5901Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo00893e
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Funding
- National Natural Science Foundation of China [21776056]
- Natural Foundation of Hebei Province (CN) [B2020202010, ZD2021026]
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This study has successfully developed a novel dearomative reaction method for the synthesis of structurally diverse tetracyclic indolines through a series of reaction steps. The reaction exhibits high yields, excellent diastereoselectivities, and good compatibility with functional groups.
A novel, highly diastereoselective palladium-catalyzed dearomative reaction of N-halobenzoyl o-haloaniline derivatives has been developed using functionalized N-tosylhydrazones as the coupling partners. This cascade dearomative protocol, which proceeds through sequential dearomative carbopalladation, migratory insertion, and beta-hydride elimination, provides a reliable and straightforward access to a wide range of structurally diverse tetracyclic indolines with C2-quaternary stereocenters in moderate to good yields and excellent diastereoselectivities with good functional group compatibility.
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