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

被引：36

作者：

Doherty, S

Newman, CR

Rath, RK

Luo, HK

Nieuwenhuyzen, M

Knight, JG

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：

ORGANIC LETTERS | 2003年 / 5卷 / 21期

关键词：

D O I：

10.1021/ol035409i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Palladium and platinum complexes of conformationally flexible 1,3-butadiene-bridged diphosphines NUPHOS can be resolved with (S)-BINOL at elevated temperatures to afford diastereopure delta-[(NUPHOS)M{(S)-BINOL}] (M = Pd, Pt). The homochiral Lewis acid complexes delta-[(NUPHOS)M]-[OTf](2), generated by protonation of delta-[(NUPHOS)M{(S)-BINOL}] with trifluoromethanesulfonic acid, catalyze the Dlels-Alder reaction between acryloyl-N-oxazolidinones and cyclopentadiene to give ee values up to 96%. The corresponding enantiopure dichlorides delta-[(NUPHOS)PtCl2] react with AgClO4 to form highly efficient catalysts that give good endo/exo selectivities and high endo enantioselectivity.

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页码：3863 / 3866

页数：4

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