New chiral ligands from isosorbide: application in asymmetric transfer hydrogenation

被引：26

作者：

Guillarme, Stephane ^{[1
]}

Nguyen, Thi Xuan Mai ^{[1
]}

Saluzzo, Christine ^{[1
]}

机构：

[1] Univ Maine, UCO2M UMR CNRS 6011, F-72085 Le Mans 09, France

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 12期

关键词：

D O I：

10.1016/j.tetasy.2008.05.033

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

New chiral beta-amino alcohols have been designed and synthesized from isosorbide, a by-product from the starch industry. These new ligands have been synthesized in three steps from isosorbide in good yields and have been used in asymmetric transfer hydrogenation reaction with Run complexes. One of these catalysts also demonstrated good catalytic activity and good enantioselectivity. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1450 / 1454

页数：5

共 72 条

[1] Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones: Mechanism and origin of enantioselectivity [J].

Alonso, DA ;

Brandt, P ;

Nordin, SJM ;

Andersson, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9580-9588

[2] (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

[3] 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

[4]

[Anonymous], 2002, CURRENT TRENDS POLYM

[5] ASYMMETRIC-SYNTHESIS BY CHIRAL RUTHENIUM COMPLEXES .4. REDUCTION OF CARBON-CARBON DOUBLE-BONDS IN PROCHIRAL ALPHA,BETA-UNSATURATED CARBOXYLIC-ACIDS BY HYDROGEN TRANSFER CATALYZED BY H4RU4(CO)8[(-)-DIOP]2 [J].

BIANCHI, M ;

MATTEOLI, U ;

MENCHI, G ;

FREDIANI, P ;

PIACENTI, F ;

BOTTEGHI, C .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 195 (03) :337-346

[6]

BIJU P, 2001, POLYM INT, V50, P1318

[7] Origin of enantioselectivity in the Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones [J].

Brandt, P ;

Roth, P ;

Andersson, PG .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :4885-4890

[8] Synthesis and characterization of new polyamides derived from di(4-cyanophenyl)isosorbide [J].

Caouthar, A. ;

Roger, P. ;

Tessier, M. ;

Chatti, S. ;

Blais, J. C. ;

Bortolussi, M. .

EUROPEAN POLYMER JOURNAL, 2007, 43 (01) :220-230

[9] Cyclic and noncyclic polycarbonates of isosorbide (1,4:3,6-dianhydro-D-glucitol) [J].

Chatti, Saber ;

Schwarz, Gert ;

Kricheldorf, Hans R. .

MACROMOLECULES, 2006, 39 (26) :9064-9070

[10] Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes [J].

Clapham, SE ;

Hadzovic, A ;

Morris, RH .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2201-2237

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