Chiral-at-Metal Octahedral Iridium Catalyst for the Asymmetric Construction of an All-Carbon Quaternary Stereocenter

被引：111
作者：
Chen, Liang-An [1 ,2 ]
Tang, Xiaojuan [1 ,2 ]
Xi, Jianwei [1 ,2 ]
Xu, Weici [1 ,2 ]
Gong, Lei [1 ,2 ]
Meggers, Eric [1 ,2 ,3 ]
机构：
[1] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China
[2] Xiamen Univ, Coll Chem & Chem Engn, Dept Biol Chem, Xiamen 361005, Peoples R China
[3] Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 52期
关键词：
asymmetric catalysis; chirality; hydrogen bonds; iridium; quaternary stereocenter; FRIEDEL-CRAFTS ALKYLATION; ENANTIOSELECTIVE CONSTRUCTION; STEREOGENIC CENTERS; CONJUGATE ADDITION; BOND DONORS; COMPLEXES; ORGANOCATALYSIS; HYDROGENATION; NITROALKENES; POTASSIUM;
D O I：
10.1002/anie.201306997
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Metal-templated organocatalysis: The enantioselective formation of an all-carbon quaternary stereocenter is catalyzed by the ligand sphere of an inert bis-cyclometalated iridium complex (see picture). In this complex, the metal-centered chirality serves as the sole source for the effective asymmetric induction. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：14021 / 14025
页数：5
相关论文
共 68 条
[1]  
[Anonymous], 2013, ANG CHEM
[2]   Catalytic Asymmetric Synthesis of Mixed 3,3′-Bisindoles and Their Evaluation as Wnt Signaling Inhibitors [J].
Arai, Takayoshi ;
Yamamoto, Yushi ;
Awata, Atsuko ;
Kamiya, Kentaro ;
Ishibashi, Masami ;
Arai, Midori A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (09) :2486-2490
[3]   Chiral-at-metal complexes and their catalytic applications in organic synthesis [J].
Bauer, Eike B. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) :3153-3167
[4]   Organocatalytic Formation of Quaternary Stereocenters [J].
Bella, Marco ;
Gasperi, Tecla .
SYNTHESIS-STUTTGART, 2009, (10) :1583-1614
[5]   Asymmetric synthesis of cyanohydrins catalysed by a potassium Δ-bis[N-salicylidene-(R)-tryptophanato]cobaltate complex [J].
Belokon, YN ;
Bulychev, AG ;
Maleev, VI ;
North, M ;
Malfanov, IL ;
Ikonnikov, NS .
MENDELEEV COMMUNICATIONS, 2004, 14 (06) :249-250
[6]   Anionic chiral cobalt(III) complexes as catalysts of asymmetric synthesis of cyanohydrins [J].
Belokon, Yu. N. ;
Maleev, V. I. ;
Mal'fanov, I. L. ;
Savel'eva, T. F. ;
Ikonnikov, N. S. ;
Bulychev, A. G. ;
Usanov, D. L. ;
Kataev, D. A. ;
North, M. .
RUSSIAN CHEMICAL BULLETIN, 2006, 55 (05) :821-827
[7]   Potassium and silver chiral cobaltate(III) complexes as precatalysts for asymmetric C-C bond formation [J].
Belokon, Yuri N. ;
Maleev, Viktor I. ;
Kataev, Dimitri A. ;
Mal'fanov, Ilya. L. ;
Bulychev, Alexander G. ;
Moskalenko, Margarita A. ;
Saveleva, Tat'yana F. ;
Skrupskaya, Tat'yana V. ;
Lyssenko, Konstantin A. ;
Godovikov, Ivan A. ;
North, Michael .
TETRAHEDRON-ASYMMETRY, 2008, 19 (07) :822-831
[8]   Chiral ion pairs in catalysis: lithium salts of chiral metallocomplex anions as catalysts for asymmetric C-C bond formation [J].
Belokon', Yuri N. ;
Maleev, Victor I. ;
Kataev, Dmitri A. ;
Saveleva, Tatiana F. ;
Skrupskaya, Tatiana V. ;
Nelyubina, Yulia V. ;
North, Michael .
TETRAHEDRON-ASYMMETRY, 2009, 20 (15) :1746-1752
[9]   Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis [J].
Bencivenni, Giorgio ;
Galzerano, Patrizia ;
Mazzanti, Andrea ;
Bartoli, Giuseppe ;
Melchiorre, Paolo .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (48) :20642-20647
[10]   Organocatalyzed enantioselective synthesis of nitroalkanes bearing all-carbon quaternary stereogenic centers through conjugate addition of acetone cyanohydrin [J].
Bernardi, Luca ;
Fini, Francesco ;
Fochi, Mariafrancesca ;
Ricci, Alfredo .
SYNLETT, 2008, (12) :1857-1861
1234567