Recent Advances in the Oxidative Coupling Reaction of Enol Derivatives

被引:6
作者
Chen, Wei [1 ,2 ]
Liu, Qiang [1 ]
机构
[1] Southern Med Univ, Sch Chinese Med, Guangzhou 510515, Peoples R China
[2] Guangdong Macau Tradit Chinese Med Technol Ind Pk, Zhuhai 519031, Guangdong, Peoples R China
基金
中国博士后科学基金;
关键词
oxidative coupling reaction; enol derivatives; carbon-carbon bond; methodology; natural product; ENANTIOSELECTIVE TOTAL-SYNTHESIS; CARBON BOND FORMATION; KETONE; 1,4-DIKETONES; DIMERIZATION; LOMAIVITICIN; ALDEHYDES; ENAMINES; ETHERS; ESTERS;
D O I
10.6023/cjoc202104058
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidative coupling reaction of enol derivatives (enolates, enol silanes, enamines, etc.) provides an efficient method for the direct construction of carbon-carbon bond, which plays a prominent role in the field of synthetic chemistry. Although the first case of this reaction had been reported in 1935, it was not until the 1970s that chemists began to pay more attention to this reaction. However, the effectiveness and practicability of this reaction were still somewhat limited at that time. In recent years, this reaction has been developed rapidly in the field of synthetic methodology and the total synthesis of natural products. Therefore, these advances in methodologies and its applications in the total synthesis of natural products in the last decades are mainly summarized.
引用
收藏
页码:3414 / 3430
页数:17
相关论文
共 115 条
[1]   Vanadium(V)-Induced Oxidative Cross-Coupling of Various Boron and Silyl Enolates [J].
Amaya, Toru ;
Osafune, Yuma ;
Maegawa, Yusuke ;
Hirao, Toshikazu .
CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (12) :1301-1304
[2]   Selective Intermolecular Oxidative Cross-Coupling of Enolates [J].
Amaya, Toru ;
Maegawa, Yusuke ;
Masuda, Takaya ;
Osafune, Yuma ;
Hirao, Toshikazu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (32) :10072-10075
[3]   Oxovanadium(V)-induced diastereoselective oxidative homocoupling of boron enolates [J].
Amaya, Toru ;
Masuda, Takaya ;
Maegawa, Yusuke ;
Hirao, Toshikazu .
CHEMICAL COMMUNICATIONS, 2014, 50 (18) :2279-2281
[4]   Diastereoselective Oxidative Carbon-Carbon Bond Formation via Silyl Bis-enol Ethers [J].
Avetta, Christopher T., Jr. ;
Konkol, Leah C. ;
Taylor, Carla N. ;
Dugan, Karen C. ;
Stern, Charlotte L. ;
Thomson, Regan J. .
ORGANIC LETTERS, 2008, 10 (24) :5621-5624
[5]   SYNTHESIS OF UNSYMMETRICAL 1,4-DIKETONES BY THE CERIC AMMONIUM-NITRATE PROMOTED CROSS-COUPLING OF TRIMETHYLSILYL ENOL ETHERS [J].
BACIOCCHI, E ;
CASU, A ;
RUZZICONI, R .
TETRAHEDRON LETTERS, 1989, 30 (28) :3707-3710
[6]   Oxidative C-C bond formation in heterocyclic chemistry [J].
Baran, Phil S. ;
Ambhaikar, Narendra B. ;
Guerrero, Carlos A. ;
Hafensteiner, Benjamin D. ;
Lin, David W. ;
Richter, Jeremy M. .
ARKIVOC, 2006, :310-325
[7]   Intermolecular oxidative enolate heterocoupling [J].
Baran, Phil S. ;
DeMartino, Michael P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (42) :7083-7086
[8]   Enantioselective total synthesis of avrainvillamide and the stephacidins [J].
Baran, Phil S. ;
Hafensteiner, Benjamin D. ;
Ambhaikar, Narendra B. ;
Guerrero, Carlos A. ;
Gallagher, John D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) :8678-8693
[9]   Total synthesis of avrainvillamide (CJ-17,665) and stephacidin B [J].
Baran, PS ;
Guerrero, CA ;
Hafensteiner, BD ;
Ambhaikar, NB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (25) :3892-3895
[10]   Short, enantioselective total synthesis of Stephacidin A [J].
Baran, PS ;
Guerrero, CA ;
Ambhaikar, NB ;
Hafensteiner, BD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) :606-609