Enantioselective Synthesis of Cyclohepta[b]indoles via Pd-Catalyzed Cyclopropane C(sp3)-H Activation as a Key Step

被引：12

作者：

Haefner, Maximilian ^{[1
]}

Sokolenko, Yevhenii M. ^{[1
]}

Gamerdinger, Paul ^{[1
]}

Stempel, Erik ^{[1
]}

Gaich, Tanja ^{[1
]}

机构：

[1] Univ Konstanz, Dept Chem, Univ Str 10, D-78464 Constance, Germany

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 18期

基金：

欧洲研究理事会;

关键词：

AMBIGUINE ISONITRILES; DIRECT ARYLATION; ALKALOIDS; INDOLE; LEAVES; PLANTS; BOND;

D O I：

10.1021/acs.orglett.9b02687

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of functionalized cyclohepta[b]indoles via Pd-catalyzed cyclopropane C-H activation followed by olefination and indole-vinylcyclopropane rearrangement is reported. The design of the chiral cyclopropane precursor was such that both enantiomeric cyclohepta[b]indoles were accessed from a single compound exhibiting a "hidden" symmetry plane. The scope of the method was demonstrated by varying the substituents on the cyclopropane as well as on the heterocycle itself.

引用

页码：7370 / 7374

页数：5

共 50 条

[41] Stereospecific Pd-Catalyzed Intermolecular C(sp3)-C(sp) Cross-Coupling of Diarylmethyl Carbonates and Terminal Alkynes Under Base-Free Conditions
Tabuchi, Sho
Hirano, Koji
Miura, Masahiro
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (47) : 16823 - 16827
[42] Synthesis of Catechols from Phenols via Pd-Catalyzed Silanol-Directed C-H Oxygenation
Huang, Chunhui
Ghavtadze, Nugzar
Chattopadhyay, Buddhadeb
Gevorgyan, Vladimir
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (44) : 17630 - 17633
[43] Pd-catalyzed cross-coupling of aromatic compounds with carboxylic acids via C-H bond activation
Wu, Junliang
Hoang, Kim Le Mai
Leow, Min Li
Liu, Xue-Wei
Organic Chemistry Frontiers, 2015, 2 (05): : 502 - 505
[44] Synthesis of 3,4-Dihydroisoquinolines by a C(sp3)-H Activation/Electrocyclization Strategy: Total Synthesis of Coralydine
Chaumontet, Manon
Piccardi, Riccardo
Baudoin, Olivier
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) : 179 - 182
[45] Synthesis of Spirooxindoles from Carbamoyl Chlorides via Cyclopropyl Methine C(sp3)-H Activation Using Palladium Catalyst
Tsukano, Chihiro
Okuno, Masataka
Takemoto, Yoshiji
CHEMISTRY LETTERS, 2013, 42 (07) : 753 - 755
[46] A new and direct route to 3-fluoromethyl substituted pyrazol-4-acrylates via Pd-catalyzed C-H activation
Wang, Xiaoguang
Fang, Xiang
Xiao, Hongyuan
Gong, Dongming
Yang, Xueyan
Wu, Fanhong
TETRAHEDRON, 2013, 69 (34) : 6993 - 7000
[47] Access to Cycloalkeno[c]-Fused Pyridines via Pd-Catalyzed C(sp2)-H Activation and Cyclization of N-Acetyl Hydrazones of Acylcycloalkenes with Vinyl Azides
Nie, Biao
Wu, Wanqing
Ren, Qingyun
Wang, Zhongqing
Zhang, Ji
Zhang, Yingjun
Jiang, Huanfeng
ORGANIC LETTERS, 2020, 22 (20) : 7786 - 7790
[48] Cu-Catalyzed Direct C-H Alkylation of Polyfluoroarenes via Remote C(sp3)-H Functionalization in Carboxamides
Liu, Hong-Chao
Li, Yuke
Gong, Xiao-Ping
Niu, Zhi-Jie
Wang, Yu-Zhao
Li, Ming
Shi, Wei-Yu
Zhang, Zhe
Liang, Yong-Min
ORGANIC LETTERS, 2021, 23 (07) : 2693 - 2698
[49] Synthesis of indoles via palladium-catalyzed C-H activation of N-aryl amides followed by coupling with alkynes
Zhou, Feng
Han, Xiuling
Lu, Xiyan
TETRAHEDRON LETTERS, 2011, 52 (36) : 4681 - 4685
[50] Pd-Catalyzed C4-Olefination of Oxazoles via C-H Bond Activation: Divergent Synthesis of Functionalized Amino Alcohol and Amino Acid Derivatives
Cui, Sunliang
Wojtas, Lukasz
Antilla, Jon C.
ORGANIC LETTERS, 2011, 13 (19) : 5040 - 5043

← 1 2 3 4 5 →