Catalytic Asymmetric Electrochemical Oxidative Coupling of Tertiary Amines with Simple Ketones

被引：173

作者：

Fu, Niankai ^{[1
,2
,3
]}

Li, Longji ^{[1
,2
]}

Yang, Qi ^{[1
,2
]}

Luo, Sanzhong ^{[1
,2
,3
]}

机构：

[1] Chinese Acad Sci, Inst Chem, Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China

[2] Univ Chinese Acad Sci, Dept Chem, Beijing 10049, Peoples R China

[3] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 08期

关键词：

C-H FUNCTIONALIZATION; BETA-KETOCARBONYLS; ANODIC-OXIDATION; CROSS; ARYLATION; ALDEHYDES; BONDS; ACTIVATION; AMINATION; STRATEGY;

D O I：

10.1021/acs.orglett.7b00746

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic asymmetric electrochemical C-H functionalization of simple ketones has been developed. The transformatibn is realized by the combination of electrochemical oxidation and chiral primary amine catalysis. This Metal- and oxidant-free method furnishes diverse Cl-alkylated tetrahydroisoquinolines in high yields and with excellent enantioselectivities under very mild conditions.

引用

页码：2122 / 2125

页数：4

共 60 条

[1] Aerobic and Electrochemical Oxidative Cross-Dehydrogenative-Coupling (CDC) Reaction in an Imidazolium-Based Ionic Liquid
Basle, Olivier
Borduas, Nadine
Dubois, Pauline
Chapuzet, Jean Marc
Chan, Tak-Hang
Lessard, Jean
Li, Chao-Jun
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (27) : 8162 - 8166
[2] Bergonzini G, 2014, CHEM SCI, V5, P112, DOI [10.1039/c3sc52265b, 10.1039/C3SC52265B]
[3] Organocatalyzed α-Oxyamination of Aldehydes Using Anodic Oxidation
Bui, Nhat-Nguyen
Ho, Xuan-Huong
Mho, Sun-il
Jang, Hye-Young
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (31) : 5309 - 5312
[4] Metal- and Reagent-Free Highly Selective Anodic Cross-Coupling Reaction of Phenols
Elsler, Bernd
Schollmeyer, Dieter
Dyballa, Katrin Marie
Franke, Robert
Waldvogel, Siegfried R.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (20) : 5210 - 5213
[5] Redox catalysis in organic electrosynthesis: basic principles and recent developments
Francke, Robert
Little, R. Daniel
[J]. CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) : 2492 - 2521
[6] Practical Electrochemical Anodic Oxidation of Polycyclic Lactams for Late Stage Functionalization
Frankowski, Kevin J.
Liu, Ruzhang
Milligan, Gregory L.
Moeller, Kevin D.
Aube, Jeffrey
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (36) : 10555 - 10558
[7] Chiral Primary Amine Catalyzed Enantioselective Protonation via an Enamine Intermediate
Fu, Niankai
Zhang, Long
Li, Jiuyuan
Luo, Sanzhong
Cheng, Jin-Pei
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (48) : 11451 - 11455
[8] Enantioselective Oxidative Cross-Coupling Reaction of 3-Indolylmethyl C-H Bonds with 1,3-Dicarbonyls Using a Chiral Lewis Acid-Bonded Nucleophile to Control Stereochemistry
Guo, Chang
Song, Jin
Luo, Shi-Wei
Gong, Liu-Zhu
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) : 5558 - 5562
[9] The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C-H/Aromatic C-H Cross-Coupling
Hayashi, Ryutaro
Shimizu, Akihiro
Yoshida, Jun-ichi
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (27) : 8400 - 8403
[10] Oxidative and Enantioselective Cross-Coupling of Aldehydes and Nitromethane Catalyzed by Diphenylprolinol Silyl Ether
Hayashi, Yujiro
Itoh, Takahiko
Ishikawa, Hayato
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (17) : 3920 - 3924

← 1 2 3 4 5 6 →