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

[1] (1S,3R,4R)-2-azanorbornylmethanol, an efficient ligand for ruthenium-catalyzed asymmetric transfer hydrogenation of ketones [J].

Alonso, DA ;

Guijarro, D ;

Pinho, P ;

Temme, O ;

Andersson, PG .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2749-2751

[2] 2-azanorbornyl alcohols: Very efficient ligands for ruthenium-catalyzed asymmetric transfer hydrogenation of aromatic ketones [J].

Alonso, DA ;

Nordin, SJM ;

Roth, P ;

Tarnai, T ;

Andersson, PG ;

Thommen, M ;

Pittelkow, U .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3116-3122

[3] Evidence for a ruthenium dihydride species as the active catalyst in the RuCl2(PPh3)-catalyzed hydrogen transfer reaction in the presence of base [J].

Aranyos, A ;

Csjernyik, G ;

Szabó, KJ ;

Bäckvall, JE .

CHEMICAL COMMUNICATIONS, 1999, (04) :351-352

[4] RUTHENIUM-CATALYZED AEROBIC OXIDATION OF ALCOHOLS VIA MULTISTEP ELECTRON-TRANSFER [J].

BACKVALL, JE ;

CHOWDHURY, RL ;

KARLSSON, U .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (07) :473-475

[5] Structure of the diamine-Rh(I) precursor in the asymmetric hydride transfer reduction of ketones: A theoretical and experimental approach [J].

Bernard, M ;

Guiral, V ;

Delbecq, F ;

Fache, F ;

Sautet, P ;

Lemaire, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (07) :1441-1446

[6] Enantioselective catalysis.: Part 143:: Astonishingly high enantioselectivity in the transfer hydrogenation of acetophenone with 2-propanol using Ru complexes of the Schiff base derived from (S)-2-amino-2-hydroxy-1,1′-binaphthyl (NOBIN) and 2-pyridinecarbaldehyde [J].

Brunner, H ;

Henning, F ;

Weber, M .

TETRAHEDRON-ASYMMETRY, 2002, 13 (01) :37-42

[7] Modular phospholane ligands in asymmetric catalysis [J].

Burk, MJ .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :363-372

[8] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S ;

CHEN, CP ;

SINGH, VK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926

[9] 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

[10] A ruthenium(II) complex with a C-2-symmetric diphosphine/diamine tetradentate ligand for asymmetric transfer hydrogenation of aromatic ketones [J].

Gao, JX ;

Ikariya, T ;

Noyori, R .

ORGANOMETALLICS, 1996, 15 (04) :1087-1089

← 1 2 3 4 →