Asymmetric transfer hydrogenation of ketones promoted by manganese(I) pre-catalysts supported by bidentate aminophosphines

被引:39
作者
Azouzi, Karim [1 ]
Bruneau-Voisine, Antoine [1 ,2 ]
Vendier, Laure [1 ]
Sortais, Jean-Baptiste [1 ,3 ]
Bastin, Stephanie [1 ]
机构
[1] Univ Toulouse, UPS, CNRS, LCC CNRS, Toulouse, France
[2] Univ Rennes, CNRS, ISCR, UMR 6226, F-35000 Rennes, France
[3] Inst Univ France, 1 Rue Descartes, F-75231 Paris 05, France
关键词
Manganese; Chiral aminophosphine ligands; Transfer hydrogenation; Reduction; Ketones; ENANTIOSELECTIVE HYDROGENATION; METAL-COMPLEXES; IRON; RUTHENIUM; ALDEHYDES;
D O I
10.1016/j.catcom.2020.106040
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A series of commercially available chiral amino-phosphines, in combination with Mn(CO)(5)Br, has been evaluated for the asymmetric reduction of ketones, using isopropanol as hydrogen source. With the most selective ligand, the corresponding manganese complex was synthesized and fully characterized. A series of ketones (20 examples) was hydrogenated in the presence of 0.5 mol% of the manganese pre-catalyst at 30 degrees C, affording the chiral alcohols in high yields with enantiomeric excesses up to 99%.
引用
收藏
页数:6
相关论文
共 35 条
[1]   Hydride Transfer Reactions Catalyzed by Cobalt Complexes [J].
Ai, Wenying ;
Zhong, Rui ;
Liu, Xufang ;
Liu, Qiang .
CHEMICAL REVIEWS, 2019, 119 (04) :2876-2953
[2]  
[Anonymous], 2006, The Handbook of Homogeneous Hydrogenation
[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]   Transfer Hydrogenation of Carbonyl Derivatives Catalyzed by an Inexpensive Phosphine-Free Manganese Precatalyst [J].
Bruneau-Voisine, Antoine ;
Wang, Ding ;
Dorcet, Vincent ;
Roisnel, Thierry ;
Darcel, Christophe ;
Sortais, Jean-Baptiste .
ORGANIC LETTERS, 2017, 19 (13) :3656-3659
[5]   Phosphine-NHC Manganese Hydrogenation Catalyst Exhibiting a Non-Classical Metal-Ligand Cooperative H2 Activation Mode [J].
Buhaibeh, Ruqaya ;
Filippov, Oleg A. ;
Bruneau-Voisine, Antoine ;
Willot, Jeremy ;
Duhayon, Carine ;
Valyaev, Dmitry A. ;
Lugan, Noel ;
Canac, Yves ;
Sortais, Jean-Baptiste .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (20) :6727-6731
[6]   Ferrocene-based aminophosphine ligands in the Ru(II)-catalysed asymmetric hydrogenation of ketones: assessment of the relative importance of planar versus carbon-centred chirality [J].
Chen, Weiping ;
Mbafor, William ;
Roberts, Stanley M. ;
Whittall, John .
TETRAHEDRON-ASYMMETRY, 2006, 17 (08) :1161-1164
[7]   Asymmetric catalysis using iron complexes - 'Ruthenium Lite'? [J].
Darwish, Muftah ;
Wills, Martin .
CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (02) :243-255
[8]   Asymmetric Transfer Hydrogenation of Ketones with Well-Defined Manganese(I) PNN and PNNP Complexes [J].
Demmans, Karl Z. ;
Olson, Maxwell E. ;
Morris, Robert H. .
ORGANOMETALLICS, 2018, 37 (24) :4608-4618
[9]   Selective Catalytic Hydrogenations of Nitriles, Ketones, and Aldehydes by Well-Defined Manganese Pincer Complexes [J].
Elangovan, Saravanakumar ;
Topf, Christoph ;
Fischer, Steffen ;
Jiao, Haijun ;
Spannenberg, Anke ;
Baumann, Wolfgang ;
Ludwig, Ralf ;
Junge, Kathrin ;
Beller, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (28) :8809-8814
[10]   Enantioselective Hydrogenation of Ketones using Different Metal Complexes with a Chiral PNP Pincer Ligand [J].
Garbe, Marcel ;
Wei, Zhihong ;
Tannert, Bianca ;
Spannenberg, Anke ;
Jiao, Haijun ;
Bachmann, Stephan ;
Scalone, Michelangelo ;
Junge, Kathrin ;
Beller, Matthias .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (08) :1913-1920