A comparison of phosphaferrocene and phospharuthenocene ligands in Rh+-catalysed enamide hydrogenation reactions:: Superior performance of the phospharuthenocene

被引:29
作者
Carmichael, Duncan [1 ]
Goldet, Gabrielle
Klankermayer, Juergen
Ricard, Louis
Seeboth, Nicolas
Stankevic, Marek
机构
[1] Ecole Polytech, CNRS, Lab Heteroelements & Coordinat, F-21128 Palaiseau, France
[2] Marie Curie Sklodowska Univ, Dept Organ Chem, PL-20614 Lublin, Poland
关键词
enamides; enantioselectivity; hydrogenation; metallocenes; phosphorus heterocycles;
D O I
10.1002/chem.200601715
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantiopure Cp*-substituted 3,4-dimethyl-5-phenylphosphametallo-cene-2-methanols (M=Fe, Ru) have been prepared from the corresponding 2-carboxy-(-)-menthylphospholide anion and elaborated into 2-CH2PPh2 phosphametallocenes (13: M=Fe; 14: M=Ru) and 2-CH2PtBuR substituted phospharuthenocenes (R=tBu, Me). The crystal structures of complexes [Rh(1,5-cod)(eta(2)-L)]+BF4- (L=13, 14) reveal significantly different aryl group configurations. Comparative studies of the hydrogenation of para-substituted N-acetylcinnamate esters with these pre-catalysts show a superior performance for the phospharuthenocene derivative in terms of both rate and enantioselectivity.
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页码:5492 / 5502
页数:11
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