Enantioselective Di-/Perfluoroalkylation of β-Ketoesters Enabled by Cooperative Photoredox/Nickel Catalysis

被引：71
作者：
Liu, Jing [1 ]
Ding, Wei [1 ]
Zhou, Quan-Quan [1 ]
Liu, Dan [1 ]
Lu, Liang-Qu [1 ]
Xiao, Wen-Jing [1 ,2 ]
机构：
[1] Cent China Normal Univ, Coll Chem, Hubei Int Sci & Technol Cooperat Base Pesticide &, Key Lab Pesticide & Chem Biol,Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 02期
基金：
中国国家自然科学基金;
关键词：
TRANSFER RADICAL-ADDITION; ASYMMETRIC TRIFLUOROMETHYLATION; SELECTIVE DIFLUOROALKYLATION; ALPHA-TRIFLUOROMETHYLATION; MERGING PHOTOREDOX; LIGHT; FLUORINATION; ALKENES; ALDEHYDES; PERFLUOROALKYLATION;
D O I：
10.1021/acs.orglett.7b03826
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Efficient and enantioselective radical difluoroalkylation and perfluoroalkylation reactions of beta-ketoesters were successfully developed through an asymmetric photoredox and nickel catalysis cascade. This protocol provides R-f-containing quaternary stereocenters in up to 67% yield and 95:5 er with ethyl iododifluoroacetate and perfluoroalkyl iodides (C3F7I and C4F9I) as radical sources under extremely mild conditions.
引用
收藏
页码：461 / 464
页数：4
相关论文
共 63 条
[1]   The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes [J].
Allen, Anna E. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) :4986-+
[2]   Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols [J].
Arai, Yusuke ;
Tomita, Ren ;
Ando, Gaku ;
Koike, Takashi ;
Akita, Munetaka .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (04) :1262-1265
[3]   Catalytic Enantioselective Synthesis of Highly Functionalized Difluoromethylated Cyclopropanes [J].
Bos, Maxence ;
Huang, Wei-Sheng ;
Poisson, Thomas ;
Pannecoucke, Xavier ;
Charette, Andre B. ;
Jubault, Philippe .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (43) :13319-13323
[4]   Carbon-Carbon Bond-Forming Reductive Elimination from Isolated Nickel(III) Complexes [J].
Bour, James R. ;
Camasso, Nicole M. ;
Meucci, Elizabeth A. ;
Kampf, Jeff W. ;
Canty, Allan J. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (49) :16105-16111
[5]   Enantioselective Catalysis of Photochemical Reactions [J].
Brimioulle, Richard ;
Lenhart, Dominik ;
Maturi, Mark M. ;
Bach, Thorsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) :3872-3890
[6]   Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors [J].
Corbett, JW ;
Ko, SS ;
Rodgers, JD ;
Gearhart, LA ;
Magnus, NA ;
Bacheler, LT ;
Diamond, S ;
Jeffrey, S ;
Klabe, RM ;
Cordova, BC ;
Garber, S ;
Logue, K ;
Trainor, GL ;
Anderson, PS ;
Erickson-Viitanen, SK .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (10) :2019-2030
[7]   Highly Enantioselective Copper-Catalyzed Electrophilic Trifluoromethylation of β-Ketoesters [J].
Deng, Qing-Hai ;
Wadepohl, Hubert ;
Gade, Lutz H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (26) :10769-10772
[8]   The Synthesis of a New Class of Chiral Pincer Ligands and Their Applications in Enantioselective Catalytic Fluorinations and the Nozaki-Hiyama-Kishi Reaction [J].
Deng, Qing-Hai ;
Wadepohl, Hubert ;
Gade, Lutz H. .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (52) :14922-14928
[9]   Bifunctional Photocatalysts for Enantioselective Aerobic Oxidation of β-Ketoesters [J].
Ding, Wei ;
Lu, Liang-Qiu ;
Quan-Quan Zhou ;
Wei, Yi ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (01) :63-66
[10]   Photocatalytic aerobic oxidation/semipinacol rearrangement sequence: a concise route to the core of pseudoindoxyl alkaloids [J].
Ding, Wei ;
Zhou, Quan-Quan ;
Xuan, Jun ;
Li, Tian-Ren ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
TETRAHEDRON LETTERS, 2014, 55 (33) :4648-4652
1234567