Efficient enantioselective hydrogenation of arylimines using aminophosphine-oxazoline iridium catalysts

被引：44

作者：

Blanc, C

Agbossou-Niedercorn, F

Nowogrocki, G

机构：

[1] ENSCL, CNRS, UMR 8010, Lab Catalyse Lille, F-59652 Villeneuve Dascq, France

[2] ENSCL, CNRS, UMR 8012, Lab Cristallog & Physicochim Solide, F-59652 Villeneuve Dascq, France

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 14期

关键词：

D O I：

10.1016/j.tetasy.2004.05.015

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The preparation and characterization of cationic iridium complexes bearing chiral aminophosphine-oxazoline auxiliaries of general formula [Ir(COD)L*]X [X: PF6 and B(Ar-F)(4)] is reported. These complexes have been applied to the asymmetric hydrogenation of two imines: N-(phenylethylidene)aniline S1 and N-(phenylethylidene)benzylamine S2 providing the corresponding chiral amines in up to 90% and 82% ee, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

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页码：2159 / 2163

页数：5

相关论文

共 52 条

[1] CHIRAL SULFONATED PHOSPHINES - SYNTHESES AND USE AS LIGANDS IN ASYMMETRIC HYDROGENATION USING AN AQUEOUS ORGANIC 2-PHASE SOLVENT SYSTEM [J].

AMRANI, Y ;

LECOMTE, L ;

SINOU, D ;

BAKOS, J ;

TOTH, I ;

HEIL, B .

ORGANOMETALLICS, 1989, 8 (02) :542-547

[2] RHODIUM(I) SULFONATED-BDPP CATALYZED ASYMMETRIC HYDROGENATION OF IMINES IN AQUEOUS ORGANIC 2-PHASE SOLVENT SYSTEMS [J].

BAKOS, J ;

OROSZ, A ;

HEIL, B ;

LAGHMARI, M ;

LHOSTE, P ;

SINOU, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (23) :1684-1685

[3] A FACILE METHOD FOR THE PREPARATION OF 2,4-BIS(DIPHENYLPHOSPHINO)PENTANE (BDPP) ENANTIOMERS AND THEIR APPLICATION IN ASYMMETRIC HYDROGENATION [J].

BAKOS, J ;

TOTH, I ;

HEIL, B ;

MARKO, L .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 279 (1-2) :23-29

[4] CATALYTIC ASYMMETRIC HYDROGENATION OF IMINES - USE OF RHODIUM(I)/PHOSPHINE COMPLEXES AND CHARACTERIZATION OF RHODIUM(I)/IMINE COMPLEXES [J].

BECALSKI, AG ;

CULLEN, WR ;

FRYZUK, MD ;

JAMES, BR ;

KANG, GJ ;

RETTIG, SJ .

INORGANIC CHEMISTRY, 1991, 30 (26) :5002-5008

[5] Chiral aminophosphine-oxazoline auxiliaries applied to copper-catalysed enantioselective 1,4-additions to enones [J].

Blanc, C ;

Agbossou-Niedercorn, F .

TETRAHEDRON-ASYMMETRY, 2004, 15 (05) :757-761

[6] Two-fold amino acid-based chiral aminophosphine-oxazolines and use in asymmetric allylic alkylation [J].

Blanc, C ;

Hannedouche, J ;

Agbossou-Niedercorn, F .

TETRAHEDRON LETTERS, 2003, 44 (34) :6469-6473

[7] Solvias Josiphos ligands: from discovery to technical applications [J].

Blaser, HU ;

Brieden, W ;

Pugin, B ;

Spindler, F ;

Studer, M ;

Togni, A .

TOPICS IN CATALYSIS, 2002, 19 (01) :3-16

[8] Selective hydrogenation for fine chemicals: Recent trends and new developments [J].

Blaser, HU ;

Malan, C ;

Pugin, B ;

Spindler, F ;

Steiner, H ;

Studer, M .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :103-151

[9]

BREUER M, 2000, ANGEW CHEM INT EDIT, V43, P788

[10] New amidophosphine-phosphinites (tLANOPs) as chiral ligands for asymmetric hydrogenation reactions [J].

Broger, EA ;

Burkart, W ;

Hennig, M ;

Scalone, M ;

Schmid, R .

TETRAHEDRON-ASYMMETRY, 1998, 9 (22) :4043-4054

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