Rhodium(III)-Catalyzed Synthesis of Spiropiperidine Derivatives via C-H Activation

被引：12

作者：

Peneau, Augustin ^{[1
]}

Retailleau, Pascal ^{[1
]}

Guillou, Catherine ^{[1
]}

Chabaud, Laurent ^{[1
]}

机构：

[1] Univ Paris Saclay, Univ Paris Sud, CNRS UPR 2301, Inst Chim Subst Nat, 1 Av Terrasse, F-91198 Gif Sur Yvette, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 04期

关键词：

INTRAMOLECULAR ANNULATION; FUNCTIONALIZATION; POTENT; AMIDOARYLATION; HYDROARYLATION; DISCOVERY; PATHWAYS; INDOLES; ALKENES; ALKYNES;

D O I：

10.1021/acs.joc.7b03252

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Spiropiperidine derivatives, an important class of bioactive molecules, were synthesized under mild conditions by rhodium(III)-catalyzed intramolecular ArC-H activation. This reaction provides a novel route to highly substituted tricyclic spiropiperidines in good to excellent yields. Under acidic conditions the resulting enamines reacted with pendant amides to afford spiropiperidines derivatives possessing an original tetracyclic structure.

引用

页码：2324 / 2340

页数：17

共 50 条

[41] Rhodium(III)-catalyzed annulative coupling between arenes and sulfoxonium ylides via C-H activation
Zheng, Guangfan
Tian, Miaomiao
Xu, Youwei
Chen, Xiaohong
Li, Xingwei
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (06): : 998 - 1002
[42] Rhodium(III)-Catalyzed Addition of Indoles with Boc-Imines via C-H Bond Activation
Wang, Jinfang
Wang, Hui
Yue, Chuanjun
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2018, 29 (06) : 1175 - 1182
[43] Rhodium(III)-Catalyzed C-H Activation of Nitrones and Annulative Coupling with Nitroalkenes
Bai, Dachang
Jia, Qingqian
Xu, Teng
Zhang, Qiuqiu
Wu, Fen
Ma, Chaorui
Liu, Bingxian
Chang, Junbiao
Li, Xingwei
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (18) : 9877 - 9884
[44] Mild Rhodium(III)-Catalyzed C-H Activation and Intermolecular Annulation with Allenes
Wang, Honggen
Glorius, Frank
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (29) : 7318 - 7322
[45] Rhodium(III)-Catalyzed Cyclopropanation of Unactivated Olefins Initiated by C-H Activation
Phipps, Erik J. T.
Piou, Tiffany
Rovis, Tomislav
SYNLETT, 2019, 30 (15) : 1787 - 1790
[46] DFT studies on rhodium(iii)-catalyzed synthesis of indanones from N-methoxybenzamides via C-H activation reaction
Li, Qianqian
Wei, Meiju
NEW JOURNAL OF CHEMISTRY, 2022, 46 (34) : 16576 - 16583
[47] Rh(iii)-Catalyzed acylation of heteroarenes with cyclobutenones via C-H/C-C bond activation
Cui, Yixin
Bai, Dachang
Liu, Bingxian
Chang, Junbiao
Li, Xingwei
CHEMICAL COMMUNICATIONS, 2020, 56 (100) : 15631 - 15634
[48] Rh(III)-catalyzed C-7 arylation of indolines with arylsilanes via C-H activation
Luo, Haiqing
Xie, Qi
Sun, Kai
Deng, Jianbo
Xu, Lin
Wang, Kejun
Luo, Xuzhong
RSC ADVANCES, 2019, 9 (32) : 18191 - 18195
[49] Rhodium(III)-catalyzed intramolecular annulation through C-H activation: concise synthesis of rosettacin and oxypalmatime
Song, Liangliang
Tian, Guilong
He, Yi
Van der Eycken, Erik V.
CHEMICAL COMMUNICATIONS, 2017, 53 (92) : 12394 - 12397
[50] Rhodium(III)-Catalyzed Sequential Cyclization of Enaminones with 1,3-Dienes via C-H Activation for the Synthesis of Fluorenones
Gao, Lei
Wang, Min
Ren, Hongwei
Yao, Jinzhong
Miao, Maozhong
Zhou, Hongwei
JOURNAL OF ORGANIC CHEMISTRY, 2024, 90 (01) : 116 - 123

← 1 2 3 4 5 →