Spirooxindole synthesis via palladium-catalyzed dearomative reductive-Heck reaction

被引:59
作者
Liu, Ren-Rong [1 ]
Xu, Yang [1 ]
Liang, Ren-Xiao [1 ]
Xiang, Bin [1 ]
Xie, Hu-Jun [2 ]
Gao, Jian-Rong [1 ]
Jia, Yi-Xia [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Gongshang Univ, Dept Appl Chem, Hangzhou 310035, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
INTRAMOLECULAR DEAROMATIZATION; ASYMMETRIC DEAROMATIZATION; HIGHLY EFFICIENT; INDOLES; OXINDOLES; DERIVATIVES; CONSTRUCTION; CYCLIZATION; ARYLATION; FUNCTIONALIZATION;
D O I
10.1039/c7ob00146k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed intramolecular dearomative reductive-Heck reaction of C2- substituted indoles is developed, which provides access to structurally diverse 3,2'-spiropyrrolidine oxindoles. By changing the hydride source to AcONa base, direct C3-arylation products [2,3-b] quinolinones are achieved in good yields. The reaction of C2-substituted benzofuran is also realized, delivering the desired spiro-product.
引用
收藏
页码:2711 / 2715
页数:5
相关论文
共 53 条
[1]   Catalytic Functionalization of Indoles in a New Dimension [J].
Bandini, Marco ;
Eichholzer, Astrid .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644
[2]  
Bedford R. B., 2009, J AM CHEM SOC, P4832
[3]   Remarkably reactive dihydroindoloindoles via palladium-catalysed dearomatisation [J].
Bedford, Robin B. ;
Fey, Natalie ;
Haddow, Mairi F. ;
Sankey, Rosalind F. .
CHEMICAL COMMUNICATIONS, 2011, 47 (12) :3649-3651
[4]   Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].
Cacchi, S ;
Fabrizi, G .
CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920
[5]   Update 1 of: Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions [J].
Cacchi, Sandro ;
Fabrizi, Giancarlo .
CHEMICAL REVIEWS, 2011, 111 :PR215-PR283
[6]   Catalytic Asymmetric Michael Addition/Cyclization of Isothiocyanato Oxindoles: Highly Efficient and Versatile Approach for the Synthesis of 3,2'-Pyrrolidinyl Mono- and Bi-spirooxindole Frameworks [J].
Cao, Yi-Ming ;
Shen, Fang-Fang ;
Zhang, Fu-Ting ;
Wang, Rui .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (04) :1184-1188
[7]   Total Synthesis of (-)-Galanthamine and (-)-Lycoramine via Catalytic Asymmetric Hydrogenation and Intramolecular Reductive Heck Cyclization [J].
Chen, Ji-Qiang ;
Xie, Jian-Hua ;
Bao, Deng-Hui ;
Liu, Sheng ;
Zhou, Qi-Lin .
ORGANIC LETTERS, 2012, 14 (11) :2714-2717
[8]   Palladium-Catalyzed Intramolecular Dearomatization of Indoles via Decarboxylative Alkynyl Termination [J].
Chen, Si ;
Wu, Xin-Xing ;
Wang, Jia ;
Hao, Xin-Hua ;
Xia, Yu ;
Shen, Yi ;
Jing, Huanwang ;
Liang, Yong-Min .
ORGANIC LETTERS, 2016, 18 (16) :4016-4019
[9]   Enantioselective Total Synthesis of (+)-Hinckdentine A via a Catalytic Dearomatization Approach [J].
Douki, Kazuya ;
Ono, Hiroyuki ;
Taniguchi, Tohru ;
Shimokawa, Jun ;
Kitamura, Masato ;
Fukuyama, Tohru .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (44) :14578-14581
[10]   The asymmetric intramolecular Heck reaction in natural product total synthesis [J].
Dounay, AB ;
Overman, LE .
CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963