Enantioselective Rhodium(I)-Catalyzed [3+2] Annulations of Aromatic Ketimines Induced by Directed C?H Activations

被引:166
作者
Tran, Duc N. [1 ,2 ]
Cramer, Nicolai [1 ]
机构
[1] EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, CH-1015 Lausanne, Switzerland
[2] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
基金
欧洲研究理事会;
关键词
alkynes; annulation; asymmetric catalysis; C?H activation; rhodium; H BOND ACTIVATION; CATALYZED DIRECT ARYLATION; ORGANIC-SYNTHESIS; CARBON-HYDROGEN; INTERMOLECULAR HYDROACYLATION; REGIOSELECTIVE SYNTHESIS; BENZOIC-ACIDS; ALKYNES; FUNCTIONALIZATION; CLEAVAGE;
D O I
10.1002/anie.201105766
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Triple selectivity: Highly substituted indenylamines can be obtained with high enantioselectivity by formal [3+2] additions of aryl ketimines with internal alkynes. These rhodium(I)-catalyzed processes proceed by selective C-H activation of one of the two arene substituents, regioselective carbometalation of the alkyne, and enantioselective addition across the imine. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11098 / 11102
页数:5
相关论文
共 87 条
[21]   Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C-H bond cleavage [J].
Fukutani, Tatsuya ;
Umeda, Nobuyoshi ;
Hirano, Koji ;
Satoh, Tetsuya ;
Miura, Masahiro .
CHEMICAL COMMUNICATIONS, 2009, (34) :5141-5143
[22]   Transition metal-catalyzed C-H activation reactions: diastereoselectivity and enantioselectivity [J].
Giri, Ramesh ;
Shi, Bing-Feng ;
Engle, Keary M. ;
Maugel, Nathan ;
Yu, Jin-Quan .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3242-3272
[23]   C-H bond functionalization in complex organic synthesis [J].
Godula, K ;
Sames, D .
SCIENCE, 2006, 312 (5770) :67-72
[24]   Isoquinoline Synthesis via Rhodium-Catalyzed Oxidative Cross-Coupling/Cyclization of Aryl Aldimines and Alkynes [J].
Guimond, Nicolas ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) :12050-+
[25]   Ruthenium-catalysed ortho vinylation of aromatic ketones with alkynes;: unexpected cyclopentaannulation [J].
Harris, PWR ;
Rickard, CEF ;
Woodgate, PD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 589 (02) :168-179
[26]   The Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3-Aliphatic-Substituted Indoles and Pyrroles [J].
Huestis, Malcolm P. ;
Chan, Lina ;
Stuart, David R. ;
Fagnou, Keith .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (06) :1338-1341
[27]   An improved catalyst architecture for rhodium(III) catalyzed C-H activation and its application to pyridone synthesis [J].
Hyster, Todd K. ;
Rovis, Tomislav .
CHEMICAL SCIENCE, 2011, 2 (08) :1606-1610
[28]   Rhodium-Catalyzed Oxidative Cycloaddition of Benzamides and Alkynes via C-H/N-H Activation [J].
Hyster, Todd K. ;
Rovis, Tomislav .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (30) :10565-10569
[29]   Functionalization of Organic Molecules by Transition-Metal-Catalyzed C(sp3)-H Activation [J].
Jazzar, Rodolphe ;
Hitce, Julien ;
Renaudat, Alice ;
Sofack-Kreutzer, Julien ;
Baudoin, Olivier .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (09) :2654-2672
[30]   Intermolecular hydroacylation by transition-metal complexes [J].
Jun, Chul-Ho ;
Jo, Eun-Ae ;
Park, Jung-Woo .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (12) :1869-1881