Palladium-catalyzed asymmetric hydrogenation of simple ketones activated by Bronsted acids

被引:29
作者
Zhou, Xiao-Yu [1 ]
Wang, Duo-Sheng [2 ]
Bao, Ming [1 ]
Zhou, Yong-Gui [2 ]
机构
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China
[2] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
基金
美国国家科学基金会;
关键词
Palladium; Asymmetric hydrogenation; Bronsted acid; Simple ketones; HIGHLY ENANTIOSELECTIVE HYDROGENATION; IRIDIUM COMPLEXES; AMINO-ALCOHOLS; QUINOLINES; LIGANDS; RU; ENTRY;
D O I
10.1016/j.tetlet.2011.03.057
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Homogeneous Pd(OCOCF3)(2)/(R)-C-4-TunePhos has been successfully applied in the asymmetric hydrogenation of simple ketones activated by catalytic amount of Bronsted acid with up to 88% ee. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2826 / 2829
页数:4
相关论文
共 70 条
[1]   Pd-catalyzed asymmetric hydrogenation of α-fluorinated iminoesters in fluorinated alcohol:: A new and catalytic enantioselective synthesis of fluoro α-amino acid derivatives [J].
Abe, H ;
Amii, H ;
Uneyama, K .
ORGANIC LETTERS, 2001, 3 (03) :313-315
[2]   New Benzo[h]quinoline-Based Ligands and their Pincer Ru and Os Complexes for Efficient Catalytic Transfer Hydrogenation of Carbonyl Compounds [J].
Baratta, Walter ;
Ballico, Maurizio ;
Baldino, Salvatore ;
Chelucci, Giorgio ;
Herdtweck, Eberhardt ;
Siega, Katia ;
Magnolia, Santo ;
Rigo, Pierluigi .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (30) :9148-9160
[3]   Osmium(II) CNN pincer complexes as efficient catalysts for both asymmetric transfer and H2 hydrogenation of ketones [J].
Baratta, Walter ;
Ballico, Maurizio ;
Chelucci, Giorgio ;
Siega, Katia ;
Rigo, Pierluigi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (23) :4362-4365
[4]   Benzo[h]quinoline Pincer Ruthenium and Osmium Catalysts for Hydrogenation of Ketones [J].
Baratta, Walter ;
Fanfoni, Lidia ;
Magnolia, Santo ;
Siega, Katia ;
Rigo, Pierluigi .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2010, (09) :1419-1423
[5]   Chiral and Nonchiral [OsX2(diphosphane)(diamine)] (X: Cl, OCH2CF3) Complexes for Fast Hydrogenation of Carbonyl Compounds [J].
Baratta, Walter ;
Barbato, Cinzia ;
Magnolia, Santo ;
Siega, Katia ;
Rigo, Pierluigi .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (10) :3201-3206
[6]  
BLASER HU, 2000, APPL HOMOGENEOUS CAT
[7]   Enantioselective Pd-Catalyzed Hydrogenation of Fluorinated Imines: Facile Access to Chiral Fluorinated Amines [J].
Chen, Mu-Wang ;
Duan, Ying ;
Chen, Qing-An ;
Wang, Duo-Sheng ;
Yu, Chang-Bin ;
Zhou, Yong-Gui .
ORGANIC LETTERS, 2010, 12 (21) :5075-5077
[8]   Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture [J].
Fujii, A ;
Hashiguchi, S ;
Uematsu, N ;
Ikariya, T ;
Noyori, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2521-2522
[9]   Iron-Catalyzed Hydrogenation, Hydride Transfer, and Hydrosilylation: An Alternative to Precious-Metal Complexes? [J].
Gaillard, Sylvain ;
Renaud, Jean-Luc .
CHEMSUSCHEM, 2008, 1 (06) :505-509
[10]   Asymmetric hydrogenation of ketones catalyzed by RuII-bicp complexes [J].
Genov, DG ;
Ager, DJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (21) :2816-2819