Synthesis and evaluation of a broad range of new chiral (aminoalkyl)phosphane ligands for asymmetric hydrogen-transfer reduction of prochiral ketones

被引：14
作者：
Léautey, M
Jubault, P
Pannecoucke, X
Quirion, JC
机构：
[1] INSA, IRCOF, CNRS, Lab Hetrochim Organ, F-76821 Mont St Aignan, France
[2] Univ Rouen, F-76821 Mont St Aignan, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 19期
关键词：
amines; asymmetric catalysis; hydrogen transfer; phosphanes;
D O I：
10.1002/ejoc.200300131
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Twenty new chiral (aminoalkyl)phosphane ligands have been prepared from four enantiomerically pure advanced chiral compounds. We describe their use for asymmetric hydrogen-transfer reduction of three prochiral ketones. Enantioselectivities up to 90% were obtained. We investigated the influence on the enantioselectivity of each part of these new (aminoalkyl)phosphane ligands. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
引用
收藏
页码：3761 / 3768
页数：8
相关论文
共 36 条
[21]   Asymmetric transfer hydrogenation of alpha,beta-acetylenic ketones [J].
Matsumura, K ;
Hashiguchi, S ;
Ikariya, T ;
Noyori, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (37) :8738-8739
[22]  
Nordin SJM, 2001, CHEM-EUR J, V7, P1431, DOI 10.1002/1521-3765(20010401)7:7<1431::AID-CHEM1431>3.0.CO
[23]  
2-L
[24]   Asymmetric hydrogenation [J].
Noyori, R .
ACTA CHEMICA SCANDINAVICA, 1996, 50 (04) :380-390
[25]   Metal-ligand bifunctional catalysis: A nonclassical mechanism for asymmetric hydrogen transfer between alcohols and carbonyl compounds [J].
Noyori, R ;
Yamakawa, M ;
Hashiguchi, S .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :7931-7944
[26]  
Noyori R, 2001, ANGEW CHEM INT EDIT, V40, P40, DOI 10.1002/1521-3773(20010105)40:1<40::AID-ANIE40>3.0.CO
[27]  
2-5
[28]  
Noyori R., 1994, ASYMMETRIC CATALYSIS
[29]  
NOYORI R, 2001, ANGEW CHEM, V113, P41
[30]   α-amino acidate-Ru(II) catalysts for asymmetric transfer hydrogenation:: First utilization of α-amino acids as an efficient ligand [J].
Ohta, T ;
Nakahara, S ;
Shigemura, Y ;
Hattori, K ;
Furukawa, I .
CHEMISTRY LETTERS, 1998, (06) :491-492
1234