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Int. J. Mol. Sci. 2007, 8(6), 553-563; doi:10.3390/i8060553
Article

Asymmetric Glyoxylate-Ene Reactions Catalyzed by Chiral Pd(II) Complexes in the Ionic Liquid [bmim][PF6]

, * , ,  and
College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou, Zhejiang 310032, China
* Author to whom correspondence should be addressed.
Received: 11 May 2007 / Accepted: 15 June 2007 / Published: 22 June 2007
(This article belongs to the Special Issue Ionic Liquids)
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Abstract

The room temperature ionic liquid [bmim][PF6] was employed as the reactionmedium in the asymmetric glyoxylate-ene reaction of α-methyl styrene (4a) with ethylglyoxylate using chiral palladium(II) complexes as the catalysts. [Pd(S-BINAP)(3,5-CF3-PhCN)2](SbF6)2 (1b) showed the highest catalytic activity. Under the reaction conditionsof 40 oC, 0.5 h, and 1b/4a molar ratio of 0.05, ethyl α-hydroxy-4-phenyl-4-pentenoate wasobtained in excellent chemical yield (94 %) with high enantioselectivity (70 %). Otherα-hydroxy esters can also be obtained in high chemical yields and enantioselectitiesthrough the glyoxylate-ene reactions of alkenes with glyoxylates catalyzed by 1b in[bmim][PF6]. Moreover, the ionic liquid [bmim][PF6] which contained the palladium(II)complex could be recycled and reused several times without significant loss of the catalyticactivity.
Keywords: Ionic liquid; glyoxylate-ene reaction; palladium; chiral; 1-n-butyl-3-methyl- imidazolium hexafluorophosphate Ionic liquid; glyoxylate-ene reaction; palladium; chiral; 1-n-butyl-3-methyl- imidazolium hexafluorophosphate
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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He, X.J.; Shen, Z.L.; Mo, W.M.; Hu, B.X.; Sun, N. Asymmetric Glyoxylate-Ene Reactions Catalyzed by Chiral Pd(II) Complexes in the Ionic Liquid [bmim][PF6]. Int. J. Mol. Sci. 2007, 8, 553-563.

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