Diastereo- and Enantioselective Intramolecular C(sp3)?H Arylation for the Synthesis of Fused Cyclopentanes

被引：112

作者：

Martin, Nicolas ^{[1
]}

Pierre, Cathleen ^{[1
]}

Davi, Michael ^{[1
]}

Jazzar, Rodolphe ^{[1
]}

Baudoin, Olivier ^{[1
]}

机构：

[1] Univ Lyon 1, Inst Chim & Biochim Mol & Supramol, CPE Lyon, CNRS,UMR 5246, F-69622 Villeurbanne, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 15期

关键词：

asymmetric catalysis; C?C coupling; C?H activation; palladium; C-H ACTIVATION; QUATERNARY STEREOCENTERS; BOND FUNCTIONALIZATION; ORGANIC-SYNTHESIS; ALKANE ARYLATION; C(SP(3))-H BONDS; CHIRAL LIGANDS; DISCOVERY; INDOLINES;

D O I：

10.1002/chem.201200018

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

All C-H bonds are not equal: The intramolecular arylation of unactivated C(sp3)-H bonds in the presence of a chiral Pd/binepine catalyst allows the synthesis of fused cyclopentanes efficiently and in an diastereo- and enantioselective manner (see scheme). © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4480 / 4484

页数：5

共 50 条

[1] Pd(II)-Catalyzed Chemo-, Diastereo-, and Enantioselective C(sp3)-H Arylation to Construct Contiguous Phosphorus and Carbon Stereocenters
Wu, Le-Song
Wang, Chen-Yue
Zhou, Tao
Shi, Bing-Feng
ORGANIC LETTERS, 2024, 26 (42) : 8988 - 8992
[2] Visible-light-induced chemo-, diastereo- and enantioselective a-C(sp3)-H functionalization of alkyl silanes
Feng, Lili
Chen, Xiaofan
Guo, Ning
Zhou, Yuqiao
Lin, Lili
Cao, Weidi
Feng, Xiaoming
CHEMICAL SCIENCE, 2023, 14 (17) : 4516 - 4522
[3] Heterogeneous palladium-catalysed intramolecular C(sp3)-H α-arylation for the green synthesis of oxindoles
Salameh, Nihad
Anastasiou, Ioannis
Ferlin, Francesco
Minio, Francesco
Chen, Shaomin
Santoro, Stefano
Liu, Ping
Gu, Yanglong
Vaccaro, Luigi
MOLECULAR CATALYSIS, 2022, 522
[4] Electrochemical Intramolecular Oxidative C(sp3)-H/C(sp3)-H Coupling for the Synthesis of 4-Quinolones
Wu, Jiwei
Jin, Kejun
Wang, Ruiyou
Wang, Xingyu
Yu, Xiaoxiao
Zhong, Liangcheng
Liu, Jianguo
SYNTHESIS-STUTTGART, 2023, 55 (03): : 451 - 456
[5] Intramolecular C(sp3)-H amination
Jeffrey, Jenna L.
Sarpong, Richmond
CHEMICAL SCIENCE, 2013, 4 (11) : 4092 - 4106
[6] Highly diastereo- and enantioselective intramolecular amidation of saturated C-H bonds catalyzed by ruthenium porphyrins
Liang, JL
Yuan, SX
Huang, JS
Yu, WY
Che, CM
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (18) : 3465 - +
[7] Catalytic Enantioselective Intramolecular C(sp3)-H Amination of 2-Azidoacetamides
Zhou, Zijun
Chen, Shuming
Qin, Jie
Nie, Xin
Zheng, Xingwen
Harms, Klaus
Riedel, Radostan
Houk, K. N.
Meggers, Eric
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (04) : 1088 - 1093
[8] Enantioselective β-C(sp3)-H arylation of amides via synergistic nickel and photoredox catalysis
Zhang, Wu
Shu, Xiaomin
Huan, Leitao
Cheng, Buqing
Huo, Haohua
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (43) : 9407 - 9409
[9] Cooperative Pd/Chiral Secondary Amine Enabled Diastereo- and Enantioselective [3+2] Cycloannulation: Synthesis of Polysubstituted Cyclopentanes
Luo, Zuoqin
Gao, Limei
He, Dongqing
Tian, Yuting
Liu, Jikai
Zheng, Yongsheng
ORGANIC LETTERS, 2025, 27 (08) : 1847 - 1852
[10] Pd(II)-Catalyzed Enantioselective C(sp3)-H Arylation of Free Carboxylic Acids
Yu, Jin-Quan (yu200@scripps.edu), 1600, American Chemical Society (140):

← 1 2 3 4 5 →