A General Protocol toward Oxindoles Bearing C3-Allylic Quaternary Stereocenter via Domino Reaction: A Concise Synthesis of Heterocycle-Fused Indoline Alkaloids
Hanxiao Yang , Ruoqian Fan , Daheng Wen , Mengmeng Fan , Weiwei Fang
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (20) : 2459 -2465.
A General Protocol toward Oxindoles Bearing C3-Allylic Quaternary Stereocenter via Domino Reaction: A Concise Synthesis of Heterocycle-Fused Indoline Alkaloids
An efficiently catalytic method toward the synthesis of indolin-2-ones featuring an allylic derived C3-quaternary stereocenter via an intramolecular Heck cyclization/Suzuki coupling of N-substituted- N-(2-bromophenyl)acrylamides and organoboron reagents was successfully developed by using a 1, 3-bis(2, 6-diisopropylphenyl)acenaphthoimidazol-2-ylidene (AnIPr)-ligated oxazoline palladacycle. It enabled a very broad substrate scope tolerating different functional groups, electronic properties and steric bulkiness. Notably, it revealed a great potential to build diverse heterocycle-fused indoline alkaloids via the same intermediate 3-allyl-1, 3-dimethylindolin-2- one.
C3-Allylic quaternary stereocenter / 3, 3’-Disubstituted oxindoles / Domino reaction / Indoline alkaloids / Molecular diversity / Nitrogen heterocycles / Organohalides / Palladacyclic N-heterocyclic carbene
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH.
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