A General Protocol toward Oxindoles Bearing C3-Allylic Quaternary Stereocenter via Domino Reaction: A Concise Synthesis of Heterocycle-Fused Indoline Alkaloids

被引：2

作者：

Yang, Hanxiao ^{[1
]}

Fan, Ruoqian ^{[1
]}

Wen, Daheng ^{[2
]}

Fan, Mengmeng ^{[1
]}

Fang, Weiwei ^{[1
]}

机构：

[1] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat Fo, Int Innovat Ctr Forest Chem & Mat, 159 Longpan Rd, Nanjing 210037, Jiangsu, Peoples R China

[2] Fudan Univ, Dept Chem, Shanghai Key Lab Mol Catalysis & Innovat Mat, Shanghai 200438, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2024年 / 42卷 / 20期

基金：

中国国家自然科学基金;

关键词：

C3-Allylic quaternary stereocenter; 3,3'-Disubstituted oxindoles; Domino reaction; Indoline alkaloids; Molecular diversity; Nitrogen heterocycles; Organohalides; Palladacyclic N-heterocyclic carbene; CATALYTIC ASYMMETRIC-SYNTHESIS; INTRAMOLECULAR HECK REACTIONS; 3-SUBSTITUTED OXINDOLES; CARBON CENTERS; PHYSOSTIGMINE; ENANTIOMER; ARYLATION;

D O I：

10.1002/cjoc.202400324

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：2459 / 2465

页数：7