Nickel-Catalyzed Enantioselective C-C Bond Formation through Csp2-O Cleavage in Aryl Esters

被引:88
作者
Cornella, Josep [1 ]
Jackson, Evan P. [1 ]
Martin, Ruben [1 ,2 ]
机构
[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
[2] Catalan Inst Res & Adv Studies ICREA, Barcelona 08010, Spain
基金
欧洲研究理事会;
关键词
aryl esters; C-O cleavage; C-O electrophiles; nickel catalysis; CROSS-COUPLING REACTIONS; ALPHA-ARYLATION; O BOND; REDUCTIVE CLEAVAGE; ACTIVATION; CONSTRUCTION; PALLADIUM; ELECTROPHILES; STRATEGY; KETONES;
D O I
10.1002/anie.201412051
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the first enantioselective C-C bond formation through C-O bond cleavage using aryl ester counterparts. This method is characterized by its wide substrate scope and results in the formation of quaternary stereogenic centers with high yields and asymmetric induction.
引用
收藏
页码:4075 / 4078
页数:4
相关论文
共 68 条
[1]   Ni-Catalyzed Reduction of Inert C-O Bonds: A New Strategy for Using Aryl Ethers as Easily Removable Directing Groups [J].
Alvarez-Bercedo, Paula ;
Martin, Ruben .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (49) :17352-17353
[2]   Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A [J].
Amaike, Kazuma ;
Muto, Kei ;
Yamaguchi, Junichiro ;
Itami, Kenichiro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13573-13576
[3]   Ligand-Free Ni-Catalyzed Reductive Cleavage of Inert Carbon-Sulfur Bonds [J].
Barbero, Nekane ;
Martin, Ruben .
ORGANIC LETTERS, 2012, 14 (03) :796-799
[4]   Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].
Bellina, Fabio ;
Rossi, Renzo .
CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146
[5]   BONDING OF AROMATIC-HYDROCARBONS TO NI(O) - STRUCTURE OF BISTRICYCLOHEXYLPHOSPHINE(1,2-ETA-2-ANTHRACENE)NICKEL(O)-TOLUENE [J].
BRAUER, DJ ;
KRUGER, C .
INORGANIC CHEMISTRY, 1977, 16 (04) :884-891
[6]  
Butoloso A. C., 2009, SYNLETT, P320
[7]   Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Cyclic Ketone Enolates: Synergetic Effect of Ligands and Barium Enolates [J].
Chen, Wenyong ;
Chen, Ming ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (45) :15825-15828
[8]  
Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[9]  
2-V
[10]  
Christoffers J., 2001, Angew. Chem, V113, P4725