Enantioselective hydrogenation of trimethylindolenine in ionic liquids

被引：38

作者：

Giernoth, R ^{[1
]}

Krumm, MS ^{[1
]}

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2004年 / 346卷 / 08期

关键词：

asymmetric catalysis; imine hydrogenation; ionic liquids; iridium; P ligands; XYLIPHOS;

D O I：

10.1002/adsc.200404050

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The enantioselective hydrogenation of trimethylindolenine (1) has been carried out in a variety of ionic liquids using an Ir-XYLIPHOS catalyst. Compared to the reaction in conventional organic media, slightly higher temperatures (50degreesC) are required, which is mainly due to the higher viscosities of the ionic media. Under these conditions we were able to identify three reaction media that gave ees comparable to the conventional process in toluene with greatly reduced reaction time (15 h as opposed to 23 h for 100% conversion; 91% conversion after 8 h). The sensitivity of the reaction system towards oxygen was also reduced significantly.

引用

页码：989 / 992

页数：4

共 17 条

[1] Solubilities and thermodynamic properties of gases in the ionic liquid 1-n-butyl-3-methylimidazolium hexafluorophosphate [J].

Anthony, JL ;

Maginn, EJ ;

Brennecke, JF .

JOURNAL OF PHYSICAL CHEMISTRY B, 2002, 106 (29) :7315-7320

[2] A STABLE CRYSTALLINE CARBENE [J].

ARDUENGO, AJ ;

HARLOW, RL ;

KLINE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363

[3]

Blaser HU, 1999, CHIMIA, V53, P275

[4] Tunable ferrocenyl diphosphine ligands for the Ir-catalyzed enantioselective hydrogenation of N-aryl imines [J].

Blaser, HU ;

Buser, HP ;

Häusel, R ;

Jalett, HP ;

Spindler, F .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 621 (1-2) :34-38

[5]

Blaser HU, 2002, ADV SYNTH CATAL, V344, P17, DOI 10.1002/1615-4169(200201)344:1<17::AID-ADSC17>3.0.CO

[6]

2-8

[7]

Cammarata L, 2001, PHYS CHEM CHEM PHYS, V3, P5192, DOI 10.1039/b106900d

[8]

CHAUVIN Y, 2002, Patent No. 200253

[9] REACTIONS OF THE NITROSONIUM ION .11. FLUORIDE TRANSFER FROM COMPLEX FLUORIDE ANIONS TO CARBENIUM IONS IN THE NITROSATIVE DECOMPOSITION OF ALIPHATIC AZIDES [J].

DOYLE, MP ;

WHITEFLEET, JL ;

BOSCH, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (16) :2923-2929

[10] METAL-COMPLEXES OF N-HETEROCYCLIC CARBENES - A NEW STRUCTURAL PRINCIPLE FOR CATALYSTS IN HOMOGENEOUS CATALYSIS [J].

HERRMANN, WA ;

ELISON, M ;

FISCHER, J ;

KOCHER, C ;

ARTUS, GRJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (21) :2371-2374

← 1 2 →