Iridium catalysts with chiral imidazole-phosphine ligands for aysmmetric hydrogenation of vinyl fluorides and other olefins

被引：71

作者：

Kaukoranta, Paivi ^{[1
]}

Engman, Mattias ^{[1
]}

Hedberg, Christian ^{[2
]}

Bergquist, Jonas ^{[3
]}

Andersson, Pher G. ^{[1
]}

机构：

[1] Dept Biochem & Organ Chem, SE-75123 Uppsala, Sweden

[2] Max Planck Inst Physiol, Dept Chem Biol, D-44227 Dortmund, Germany

[3] Dept Phys & Analyt Chem, SE-75124 Uppsala, Sweden

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 7-8期

关键词：

asymmetric hydrogenation; iridium; N; P donating ligand; vinyl fluorides;

D O I：

10.1002/adsc.200800062

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

New chiral bidentate imidazole-phosphine ligands have been prepared and evaluated for the iridium-catalysed asymmetric hydrogenation of olefins. The imidazole-phosphine-ligated iridium catalysts hydrogenated trisubstituted olefins with the same sense of enantiodiscrimination as known iridium catalysts possessing oxazole and thiazole as N-donors. The imidazole-based catalysts were shown to hydrogenate vinyl fluorides, in some cases with the highest ee values published to date.

引用

页码：1168 / 1176

页数：9

共 41 条

[1]

[Anonymous], 2001, ANGEW CHEM INT EDIT

[2]

[Anonymous], ANGEW CHEM

[3]

[Anonymous], ANGEW CHEM

[4]

Blankenstein J, 2001, ANGEW CHEM INT EDIT, V40, P4445, DOI 10.1002/1521-3773(20011203)40:23<4445::AID-ANIE4445>3.0.CO

[5]

2-V

[6] Fluorine in medicinal chemistry [J].

Böhm, HJ ;

Banner, D ;

Bendels, S ;

Kansy, M ;

Kuhn, B ;

Müller, K ;

Obst-Sander, U ;

Stahl, M .

CHEMBIOCHEM, 2004, 5 (05) :637-643

[7] New mechanistic insights into the iridium- phosphanooxazoline-catalyzed hydrogenation of unfunctionalized olefins: A DFT and kinetic study [J].

Brandt, P ;

Hedberg, C ;

Andersson, PG .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (01) :339-347

[8] New P,N Ligands for asymmetric Ir-catalyzed reactions [J].

Bunlaksananusorn, T ;

Polborn, K ;

Knochel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (33) :3941-3943

[9] The role of natural product chemistry in drug discovery [J].

Butler, MS .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (12) :2141-2153

[10] New P,N-Ferrocenyl ligands for the asymmetric ir-catalyzed hydrogenation of imines [J].

Cheemala, Murthy N. ;

Knochel, Paul .

ORGANIC LETTERS, 2007, 9 (16) :3089-3092

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