Marked enantioselectivity enhancements for Diels-Alder reactions in ionic liquids catalysed by platinum diphosphine complexes

被引：68

作者：

Doherty, S ^{[1
]}

Goodrich, P

Hardacre, C

Luo, HK

Rooney, DW

Seddon, KR

Styring, P

机构：

[1] Queens Univ Belfast, Sch Chem, Belfast BT9 5AG, Antrim, North Ireland

[2] Queens Univ Belfast, QUILL, Belfast BT9 5AG, Antrim, North Ireland

[3] Queens Univ Belfast, Sch Chem Engn, Belfast BT9 5AG, Antrim, North Ireland

[4] Univ Sheffield, Dept Chem & Proc Engn, Sheffield S1 3AD, S Yorkshire, England

来源：

GREEN CHEMISTRY | 2004年 / 6卷 / 01期

关键词：

D O I：

10.1039/b312761c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Asymmetric Diels-Alder reactions using platinum complexes of BINAP, or of conformationally flexible NUPHOS-type diphosphines, have been compared in dichloromethane and selected ionic liquids. Significant enhancements in the enantioselectivity (Deltaee approximate to 20%), as well as reaction rate, were achieved in ionic liquids compared with the organic media.

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页码：63 / 67

页数：5

相关论文

共 42 条

[1] Heterogeneously catalysed selective hydrogenation reactions in ionic liquids [J].

Anderson, K ;

Goodrich, P ;

Hardacre, C ;

Rooney, DW .

GREEN CHEMISTRY, 2003, 5 (04) :448-453

[2] Ionic liquids and chirality: opportunities and challenges [J].

Baudequin, C ;

Baudoux, J ;

Levillain, J ;

Cahard, D ;

Gaumont, AC ;

Plaquevent, JC .

TETRAHEDRON-ASYMMETRY, 2003, 14 (20) :3081-3093

[3] Asymmetric catalysis with the normally unresolvable, conformationally dynamic 2,2′-bis(diphenylphosphino)-1,1′-biphenyl (biphep) [J].

Becker, JJ ;

White, PS ;

Gagné, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9478-9479

[4] Hydrophobic, highly conductive ambient-temperature molten salts [J].

Bonhote, P ;

Dias, AP ;

Papageorgiou, N ;

Kalyanasundaram, K ;

Gratzel, M .

INORGANIC CHEMISTRY, 1996, 35 (05) :1168-1178

[5] Catalytic asymmetric dihydroxylation of olefins using a recoverable and reusable OsO42- in ionic liquid [bmim][PF6] [J].

Branco, LC ;

Afonso, CAM .

CHEMICAL COMMUNICATIONS, 2002, (24) :3036-3037

[6] The Heck reaction in ionic liquids: A multiphasic catalyst system [J].

Carmichael, AJ ;

Earle, MJ ;

Holbrey, JD ;

McCormac, PB ;

Seddon, KR .

ORGANIC LETTERS, 1999, 1 (07) :997-1000

[7] Copper(I) mediated living radical polymerisation in an ionic liquid [J].

Carmichael, AJ ;

Haddleton, DM ;

Bon, SAF ;

Seddon, KR .

CHEMICAL COMMUNICATIONS, 2000, (14) :1237-1238

[8] Molten salts (ionic liquids) to improve the activity, selectivity and stability of the palladium catalysed Trost-Tsuji C-C coupling in biphasic media [J].

de Bellefon, C ;

Pollet, E ;

Grenouillet, P .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 145 (1-2) :121-126

[9] Ruthenium complexes of the 1,4-bis(diphenylphosphino)-1,3-butadiene-bridged diphosphine 1,2,3,4-Me4-NUPHOS:: Solvent-dependent interconversion of four- and six-electron donor coordination and transfer hydrogenation activity [J].

Doherty, S ;

Newman, CR ;

Hardacre, C ;

Nieuwenhuyzen, M ;

Knight, JG .

ORGANOMETALLICS, 2003, 22 (07) :1452-1462

[10] Highly efficient asymmetric lewis acid catalysis with platinum group complexes of conformationally flexible 1,3-butadiene-bridged diphosphines, NUPHOS [J].

Doherty, S ;

Newman, CR ;

Rath, RK ;

Luo, HK ;

Nieuwenhuyzen, M ;

Knight, JG .

ORGANIC LETTERS, 2003, 5 (21) :3863-3866

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