Asymmetric Hydrogenation of Pyridinium Salts with an Iridium Phosphole Catalyst

被引:77
作者
Chang, Mingxin [1 ,2 ]
Huang, Yuhua [1 ,2 ,3 ,4 ]
Liu, Shaodong [1 ,2 ]
Chen, Yonggang [3 ,4 ]
Krska, Shane W. [3 ,4 ]
Davies, Ian W. [3 ,4 ]
Zhang, Xumu [1 ,2 ]
机构
[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
[2] Rutgers State Univ, Dept Med Chem, Piscataway, NJ 08854 USA
[3] Merck & Co Inc, Dept Proc Chem, Rahway, NJ 07065 USA
[4] Merck & Co Inc, Dept Discovery Chem, Rahway, NJ 07065 USA
基金
美国国家卫生研究院;
关键词
asymmetric catalysis; heterocycles; hydrogenation; iridium; stereoselectivity; N-IMINOPYRIDINIUM YLIDES; ENANTIOSELECTIVE HYDROGENATION; PHOTOELECTRON-SPECTROSCOPY; ACCESS;
D O I
10.1002/anie.201406762
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Iridium-catalyzed asymmetric hydrogenation of Nalkyl-2-alkylpyridinium salts provided 2-aryl-substituted piperidines with high levels of enantioselectivity. Simple benzyl and other alkyl groups successfully activated the challenging pyridine substrates toward hydrogenation. The use of the unusual chiral-phosphole-based MP2-SEGPHOS was the key to the success of this approach which provides a versatile and practical procedure for the synthesis of chiral piperidines.
引用
收藏
页码:12761 / 12764
页数:4
相关论文
共 40 条
[21]  
Legault CY, 2008, HETEROCYCLES, V76, P1271
[22]   Catalytic asymmetric hydrogenation of N-iminopyridinium ylides:: Expedient approach to enantioenriched substituted piperidine derivatives [J].
Legault, CY ;
Charette, AB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :8966-8967
[23]   Asymmetric hydrogenation of pyridines: Enantioselective synthesis of nipecotic acid derivatives [J].
Lei, Aiwen ;
Chen, Mao ;
He, Minsheng ;
Zhang, Xumu .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (19) :4343-4347
[24]   Design of Phosphorus Ligands with Deep Chiral Pockets: Practical Synthesis of Chiral β-Arylamines by Asymmetric Hydrogenation [J].
Liu, Guodu ;
Liu, Xiangqian ;
Cai, Zhihua ;
Jiao, Guangjun ;
Xu, Guangqing ;
Tang, Wenjun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (15) :4235-4238
[25]   Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation of Pyridines [J].
Liu, Yongbing ;
Du, Haifeng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (35) :12968-12971
[26]  
Nugent T. C., 2010, Chiral Amine Synthesis: Methods, Developments and Applications
[27]   Ruthenium-NHC-Catalyzed Asymmetric Hydrogenation of Indolizines: Access to Indolizidine Alkaloids [J].
Ortega, Nuria ;
Tang, Dan-Tam D. ;
Urban, Slawomir ;
Zhao, Dongbing ;
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (36) :9500-9503
[28]   Development of a Concise, Asymmetric Synthesis of a Smoothened Receptor (SMO) inhibitor: Enzymatic Transamination of a 4-Piperidinone with Dynamic Kinetic Resolution [J].
Peng, Zhihui ;
Wong, John W. ;
Hansen, Eric C. ;
Puchlopek-Dermenci, Angela L. A. ;
Clarke, Hugh J. .
ORGANIC LETTERS, 2014, 16 (03) :860-863
[29]   THEORY AND APPLICATION OF PHOTOELECTRON SPECTROSCOPY .20. DIRECT PROOF OF NONAROMATICITY OF PHOSPHOLES AND ARSOLES [J].
SCHAFER, W ;
SCHWEIG, A ;
MARKL, G ;
HAUPTMANN, H ;
MATHEY, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1973, 12 (02) :145-146
[30]   THEORY AND APPLICATION OF PHOTOELECTRON-SPECTROSCOPY .60. PHOSPHOLES - ELECTRONIC-STRUCTURE [J].
SCHAFER, W ;
SCHWEIG, A ;
MATHEY, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (02) :407-414