Fluorinated alcohols as solvents for enantioselective hydrogenation with chiral self-assembling rhodium catalysts

被引:27
作者
Dubrovina, Natalia V.
Shuklov, Ivan A.
Birkholz, Mandy-Nicole
Michalik, Dirk
Paciello, Rocco
Boerner, Armin
机构
[1] Univ Rostock e V, Leibniz Inst Katayse, D-18059 Rostock, Germany
[2] GCB O, Basic Chem Res, BASF AG, D-67056 Ludwigshafen, Germany
[3] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
关键词
asymmetric catalysis; hydrogenation; phosphane ligands; rhodium; self-assembly; solvent effects;
D O I
10.1002/adsc.200700177
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We herein describe the beneficial effect of fluorinated alcohols on asymmetric hydrogenation using chiral self-assembling rhodium complexes. Previously, the application of these catalysts has been hampered by low reaction rates in non-polar solvents, which are essential for establishing the self-assembling architecture via hydrogen bonding. Excellent reaction rates are usually observed in alcohols as solvents, but the characteristic hydrogen bonds are cleaved in those media, resulting in poor ee values. We now show for the first time that the disadvantageous properties of both solvent classes on the catalytic reaction can be overcome by using fluorinated alcohols. Due to this key finding, homogeneous catalysis with self-assembling catalysts is much closer to practical application.
引用
收藏
页码:2183 / 2187
页数:5
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