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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]

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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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