1,2-Bis(2,5-diphenylphospholano)methane, a new ligand for asymmetric hydrogenation

被引：37

作者：

Jackson, Mark ^{[1
]}

Lennon, Ian C. ^{[1
]}

机构：

[1] Dow Chem Co USA, Dowpharma, Chirotech Technol Ltd, Unit 162, Cambridge CB4 0GH, England

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 10期

关键词：

rhodium; asymmetric catalysis; hydrogenation; phospholane;

D O I：

10.1016/j.tetlet.2007.01.018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,2-Bis(2,5-diphenylphospholano)methane (Ph-BPM) has been prepared in good yield from 2,5-trans-diphenylphospholane-borane adduct. Rhodium and ruthenium complexes of this ligand have been prepared and their usefulness in asymmetric hydrogenation has been investigated. [Ph-BPM Rh(COD)]BF4 showed high activity and selectivity for itaconate and dehydroamino acid hydrogenation. Ph-BPM RUCl2(DPEN) was effective for imine hydrogenation. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：1831 / 1834

页数：4

共 13 条

[1] 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

[2] Asymmetric hydrogenation of enamides with Rh-BisP* and Rh-MiniPHOS catalysts. Scope, limitations, and mechanism [J].

Gridnev, ID ;

Yasutake, M ;

Higashi, N ;

Imamoto, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) :5268-5276

[3]

Gridnev ID, 2001, ADV SYNTH CATAL, V343, P118, DOI 10.1002/1615-4169(20010129)343:1<118::AID-ADSC118>3.0.CO

[4]

2-Z

[5] Synthesis and first applications of a new family of chiral monophosphine ligand: 2,5-diphenylphosphospholanes [J].

Guillen, F ;

Rivard, M ;

Toffano, M ;

Legros, JY ;

Daran, JC ;

Fiaud, JC .

TETRAHEDRON, 2002, 58 (29) :5895-5904

[6] Highly selective asymmetric hydrogenation using a three hindered quadrant bisphosphine rhodium catalyst [J].

Hoge, G ;

Wu, HP ;

Kissel, WS ;

Pflum, DA ;

Greene, DJ ;

Bao, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :5966-5967

[7] SYNTHESIS AND REACTIONS OF PHOSPHINE BORANES - SYNTHESIS OF NEW BIDENTATE LIGANDS WITH HOMOCHIRAL PHOSPHINE CENTERS VIA OPTICALLY PURE PHOSPHINE BORANES [J].

IMAMOTO, T ;

OSHIKI, T ;

ONOZAWA, T ;

KUSUMOTO, T ;

SATO, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5244-5252

[8] AN IMPROVED DIPHOSPHINE-IRIDIUM(I) CATALYST SYSTEM FOR THE ASYMMETRIC HYDROGENATION OF CYCLIC IMINES - PHTHALIMIDE AS AN EFFICIENT COCATALYST [J].

MORIMOTO, T ;

ACHIWA, K .

TETRAHEDRON-ASYMMETRY, 1995, 6 (11) :2661-2664

[9] Asymmetric hydrogenation of alkenyl, cyclopropyl, and aryl ketones.: RuCl2(xylbinap)(1,2-diamine) as a precatalyst exhibiting a wide scope [J].

Ohkuma, T ;

Koizumi, M ;

Doucet, H ;

Pham, T ;

Kozawa, M ;

Murata, K ;

Katayama, E ;

Yokozawa, T ;

Ikariya, T ;

Noyori, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (51) :13529-13530

[10] Expanding the family of phospholane-based ligands: 1,2-bis(2,5-diphenylphospholano)ethane [J].

Pilkington, CJ ;

Zanotti-Gerosa, A .

ORGANIC LETTERS, 2003, 5 (08) :1273-1275

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