Oxidative Enantioselective α-Fluorination of Aliphatic Aldehydes Enabled by N-Heterocyclic Carbene Catalysis

被引：60
作者：
Li, Fangyi [1 ]
Wu, Zijun [1 ]
Wang, Jian [1 ]
机构：
[1] Tsinghua Univ, Sch Med, Dept Pharmacol & Pharmaceut Sci, Beijing 100084, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 02期
关键词：
aldehydes; enolates; fluorine; N-heterocyclic carbenes; oxidation; ASYMMETRIC FLUORINATION; NHC CATALYSIS; NUCLEOPHILIC CARBENES; MEDICINAL CHEMISTRY; BETA-KETOESTERS; ACID-CHLORIDES; ORGANOCATALYSIS; ACTIVATION; TRIFLUOROMETHYLATION; COMBINATION;
D O I：
10.1002/anie.201409473
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Described is the first study on oxidative enantioselective -fluorination of simple aliphatic aldehydes enabled by N-heterocyclic carbene catalysis. N-fluorobis(phenyl)sulfonimide serves as a an oxidant and as an F source. The CF bond formation occurs directly at the position of simple aliphatic aldehydes, thus overcoming nontrivial challenges, such as competitive difluorination and nonfluorination, and proceeds with high to excellent enantioselectivities.
引用
收藏
页码：656 / 659
页数：4
相关论文
共 80 条
[1]  
[Anonymous], 2007, ANGEW CHEM
[2]   Fused polycyclic nucleophilic carbenes - synthesis, structure, and function [J].
Arduengo, Anthony J., III ;
Iconaru, Luigi I. .
DALTON TRANSACTIONS, 2009, (35) :6903-6914
[3]   Mechanistic and Computational Studies of Oxidatively-Induced Aryl-CF3 Bond-Formation at Pd: Rational Design of Room Temperature Aryl Trifluoromethylation [J].
Ball, Nicholas D. ;
Gary, J. Brannon ;
Ye, Yingda ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (19) :7577-7584
[4]  
Baudoux J., 2007, ORG REACTIONS, P347
[5]   Enantioselective organocatalytic α-fluorination of aldehydes [J].
Beeson, TD ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) :8826-8828
[6]   Extending NHC-Catalysis: Coupling Aldehydes with Unconventional Reaction Partners [J].
Biju, Akkattu T. ;
Kuhl, Nadine ;
Glorius, Frank .
ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (11) :1182-1195
[7]   Fluorine in medicinal chemistry [J].
Böhm, HJ ;
Banner, D ;
Bendels, S ;
Kansy, M ;
Kuhn, B ;
Müller, K ;
Obst-Sander, U ;
Stahl, M .
CHEMBIOCHEM, 2004, 5 (05) :637-643
[8]  
Brunet V.A., 2008, ANGEW CHEM, V120, P1198
[9]   Catalytic asymmetric fluorination comes of age [J].
Brunet, Vincent A. ;
O'Hagan, David .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (07) :1179-1182
[10]   Fluorine & chirality: how to create a nonracemic stereogenic carbon-fluorine centre? [J].
Cahard, Dominique ;
Xu, Xiuhua ;
Couve-Bonnaire, Samuel ;
Pannecoucke, Xavier .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :558-568
12345678