Highly efficient asymmetric hetero-Diels-Alder reactions of carbonyl compounds catalyzed by Lewis acid platinum complexes of conformationally flexible NUPHOS-type diphosphines

被引：26

作者：

Doherty, S

Knight, JG

Hardacre, C

Lou, HK

Newman, CR

Rath, RK

Campbell, S

Nieuwenhuyzen, M

机构：

[1] Queens Univ Belfast, Sch Chem, Ctr Theory & Applicat Catalysis, Belfast BT9 5AG, Antrim, North Ireland

[2] Newcastle Univ, Sch Nat Sci, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

ORGANOMETALLICS | 2004年 / 23卷 / 26期

关键词：

D O I：

10.1021/om049392z

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Conformationally flexible NUPHOS-type diphosphines have been resolved as their diastereopure platinum BINOLate complexes delta- and lambda-[(NUPHOS)Pt{(S)-BINOL}] and the corresponding enantiopure Lewis acids delta- and lambda-[(NUPHOS)Pt(OTf)(2)], being generated by protonation with trifluoromethanesulfonic acid, act as highly efficient catalysts for the hetero-Diels-Alder reaction of nonactivated conjugated dienes with aryl glyoxals and glyoxylate esters, giving ee's as high as 99%.

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页码：6127 / 6133

页数：7

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共 60 条

[1] Helical chirality control of palladium complexes that bear a tetrakis(phosphanyl)terphenyl ligand: Application as asymmetric Lewis acid catalysts [J].

Aikawa, K ;

Mikami, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5458-5461

[2] Atropos but achiral tris(phosphanyl)biphenyl ligands for RU-catalyzed asymmetric hydrogenation [J].

Aikawa, K ;

Mikami, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5455-5458

[3] Improved carbonylation of heterocyclic chlorides and electronically challenging aryl bromides [J].

Albaneze-Walker, J ;

Bazaral, C ;

Leavey, T ;

Dormer, PG ;

Murry, JA .

ORGANIC LETTERS, 2004, 6 (13) :2097-2100

[4] The use of achiral ligands to convey asymmetry: Chiral environment amplification [J].

Balsells, J ;

Walsh, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) :1802-1803

[5] 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

[6] Electron-poor benzonitriles as labile, stabilizing ligands in asymmetric catalysis [J].

Becker, JJ ;

Van Orden, LJ ;

White, PS ;

Gagné, MR .

ORGANIC LETTERS, 2002, 4 (05) :727-730

[7] 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

[8] 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

[9] Optimization of asymmetric catalysts using achiral ligands: Metal geometry-induced ligand asymmetry [J].

Davis, TJ ;

Balsells, J ;

Carroll, PJ ;

Walsh, PJ .

ORGANIC LETTERS, 2001, 3 (14) :2161-2164

[10] 2,2'-Bis(diphenylphosphino) biphenyl revisited [J].

Desponds, O ;

Schlosser, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 507 (1-2) :257-261

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