Asymmetric Fluorination Reactions promoted by Chiral Hydrogen Bonding-based Organocatalysts

被引:23
作者
Auria-Luna, Fernando [1 ]
Mohammadi, Somayeh [2 ]
Divar, Masoumeh [2 ]
Gimeno, M. Concepcion [3 ]
Herrera, Raquel P. [1 ]
机构
[1] Univ Zaragoza, Lab Organocatalisis Asimetr, Dept Quim Organ, Inst Sintesis Quim & Catalisis Homogenea ISQCH,CS, C Pedro Cerbuna 12, Zaragoza 50009, Spain
[2] Shiraz Univ Med Sci, Med & Nat Prod Chem Res Ctr, Shiraz 7134853734, Iran
[3] Univ Zaragoza, Dept Quim Inorgan, Inst Sintesis Quim & Catalisis Homogenea ISQCH, CSIC, C Pedro Cerbuna 12, Zaragoza 50009, Spain
关键词
fluorination; hydrogen-bond; organocatalysis; phosphoric acid; squaramide; (thio)urea; CATALYTIC ENANTIOSELECTIVE FLUORINATION; PHASE-TRANSFER CATALYSIS; BETA-KETO-ESTERS; MICHAEL ADDITION; PHOSPHORIC-ACID; CARBON-CARBON; MEDICINAL CHEMISTRY; BRONSTED ACID; CINCHONA ALKALOIDS; THIOUREA CATALYSTS;
D O I
10.1002/adsc.202000848
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Fluorinated compounds can exhibit interesting biological properties. The importance of these species has made that the chemistry of fluorine has experienced a great development. On this review, the recent advances on asymmetric fluorination reactions promoted by chiral hydrogen bonding-based organocatalysts are discussed. Hence, examples using phosphoric acid, carboxylic acid, (thio)urea and squaramide derivatives are illustrated. The growth of this field is amazing. We have only considered pivotal works in which direct fluorination takes place using a fluorinating agent, leaving aside the reactions where a fluorine atom is incorporated from the beginning as part of other reactants. Herein, the scarce existing examples on this field of research have been compiled.
引用
收藏
页码:5275 / 5300
页数:26
相关论文
共 199 条
[61]   Fluorine in medicinal chemistry: A review of anti-cancer agents [J].
Isanbor, C ;
O'Hagan, D .
JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (03) :303-319
[62]   Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles [J].
Ishimaru, Takehisa ;
Shibata, Norio ;
Horikawa, Takao ;
Yasuda, Naomi ;
Nakamura, Shuichi ;
Toru, Takeshi ;
Shiro, Motoo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4157-4161
[63]  
Jakab G, 2013, COMPREHENSIVE ENANTIOSELECTIVE ORGANOCATALYSIS: CATALYSTS, REACTIONS, AND APPLICATIONS, VOLS 1-3, P315
[64]   The unique role of fluorine in the design of active ingredients for modern crop protection [J].
Jeschke, P .
CHEMBIOCHEM, 2004, 5 (05) :570-589
[65]   Enantioseletive Fluorination of 3-Functionalized Oxindoles Using Electron-rich Amino Urea Catalyst [J].
Jiang, Xiaojian ;
Wang, Haitao ;
He, Haoquan ;
Wang, Wei ;
Wang, Yuqiang ;
Ke, Zhihai ;
Yeung, Ying-Yeung .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (24) :4710-4714
[66]  
Kampen D., 2010, TOP CURR CHEM, V291, P385
[67]  
Kanemasa S., 2005, ANGEW CHEM, V117, P4276
[68]   Primary Amine, Thiourea-Based Dual Catalysis Motif for Synthesis of Stereogenic, All-Carbon Quaternary Center-Containing Cycloalkanones [J].
Kang, Jun Yong ;
Carter, Rich G. .
ORGANIC LETTERS, 2012, 14 (12) :3178-3181
[69]   Asymmetric Mannich-type Reactions of Fluorinated Ketoesters with Binaphthyl-Modified Thiourea Catalysts [J].
Kang, Young Ku ;
Yoon, Sung Je ;
Kim, Dae Young .
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (04) :1195-1200
[70]   Catalytic enantioselective fluorination of β-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts [J].
Kim, DY ;
Park, EJ .
ORGANIC LETTERS, 2002, 4 (04) :545-547