Catalytic Asymmetric Electrochemical Oxidative Coupling of Tertiary Amines with Simple Ketones

被引：171

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 50 条

[31] Catalytic Asymmetric Oxidative γ-Coupling of α, β-Unsaturated Aldehydes with Air as the Terminal Oxidant
Naesborg, Line
Corti, Vasco
Leth, Lars Astrup
Poulsen, Pernille H.
Jorgensen, Karl Anker
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (06) : 1606 - 1610
[32] ELECTROCHEMICAL OXIDATION OF TERTIARY ALCOHOLS AND KETONES
SOKOLOVA, EI
RAICHEVA, SN
CHRISTOV, MV
ZEITSCHRIFT FUR PHYSIKALISCHE CHEMIE NEUE FOLGE, 1988, 160 : 59 - 67
[33] Catalytic dehydrogenative coupling of amines
Ainembabazi, Diana
Tiedemann, Nicholas
Voutchkova, Adelina
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
[34] Direct Catalytic Asymmetric Reductive Amination of Aliphatic Ketones Utilizing Diphenylmethanamine as Coupling Partner
Huang, Haizhou
Zhao, Yunfei
Yang, Yang
Zhou, Le
Chang, Mingxin
ORGANIC LETTERS, 2017, 19 (08) : 1942 - 1945
[35] Highly regioselective, catalytic asymmetric reductive coupling of 1,3-enynes and ketones
Miller, KM
Jamison, TF
ORGANIC LETTERS, 2005, 7 (14) : 3077 - 3080
[36] Strong and Confined Acids Enable a Catalytic Asymmetric Nazarov Cyclization of Simple Divinyl Ketones
Ouyang, Jie
Kennemur, Jennifer L.
Kanta, De Chandra
Fares, Christophe
List, Benjamin
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (08) : 3414 - 3418
[37] Phosphine-free chiral iridium catalysts for asymmetric catalytic hydrogenation of simple ketones
Kumar, Prashant
Irrgang, Torsten
Kostakis, George E.
Kempe, Rhett
RSC ADVANCES, 2016, 6 (45): : 39335 - 39342
[38] Catalytic asymmetric vinylation and dienylation of ketones
Li, HM
Walsh, PJ
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) : 8355 - 8361
[39] Catalytic asymmetric vinylation of ketones.
Li, HM
Walsh, PJ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U34 - U34
[40] OXIDATIVE DEAMINATION OF AMINES TO KETONES VIA OXAZIRIDINES
DINIZO, SE
WATT, DS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (23) : 6900 - 6901

← 1 2 3 4 5 →