Asymmetric transfer hydrogenation of imines and iminiums catalyzed by a water-soluble catalyst in water

被引：165

作者：

Wu, JS

Wang, F

Ma, YP

Cui, XC

Cun, LF

Zhu, J ^{[1
]}

Deng, JG

Yu, BL

机构：

[1] Chinese Acad Sci, Key Lab Asymmetr & Chirotechnol Sichuan Prov, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

[2] Chinese Acad Sci, Union Lab Assymmetr Synth, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

[3] Chinese Acad Sci, Grad Sch, Beijing, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2006年 / 16期

关键词：

D O I：

10.1039/b600496b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first asymmetric transfer hydrogenation of cyclic imines and iminiums in water was successfully performed in high yields and enantioselectivities with sodium formate as the hydrogen source and CTAB as an additive catalyzed by a water- soluble and recyclable ruthenium( II) complex of the ligand ( R, R)- 2.

引用

页码：1766 / 1768

页数：3

共 45 条

[1] Practical synthesis of chiral sultam auxiliaries: 3-substituted-1,2-benzisothiazoline 1,1-dioxides [J].

Ahn, KH ;

Ham, C ;

Kim, SK ;

Cho, CW .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :7047-7048

[2] 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

[3] 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

[4]

Brunel J.M., 2003, Rec. Res. Dev. Org. Chem, V7, P155

[5] Water-soluble arene ruthenium complexes containing a trans-1,2-diaminocyclohexane ligand as enantioselective transfer hydrogenation catalysts in aqueous solution [J].

Canivet, J ;

Labat, G ;

Stoeckli-Evans, H ;

Süss-Fink, G .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2005, (22) :4493-4500

[6] Reduction of Imines by hydroxycyclopentadienyl ruthenium hydride: Intramolecular trapping evidence for hydride and proton transfer outside the coordination sphere of the metal [J].

Casey, CP ;

Bikzhanova, GA ;

Cui, Q ;

Guzei, IA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (40) :14062-14071

[7] Hydrogen transfer to carbonyls and imines from a hydroxycyclopentadienyl ruthenium hydride: Evidence for concerted hydride and proton transfer [J].

Casey, CP ;

Singer, SW ;

Powell, DR ;

Hayashi, RK ;

Kavana, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (06) :1090-1100

[8] Asymmetric synthesis of isoquinoline alkaloids [J].

Chrzanowska, M ;

Rozwadowska, MD .

CHEMICAL REVIEWS, 2004, 104 (07) :3341-3370

[9] 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

[10] Enantioselective hydrogenation of imines using a diverse library of ruthenium dichloride(diphospbine)(diamine) precatalysts [J].

Cobley, CJ ;

Henschke, JP .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :195-201

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