Chiral bis(oxazoline)-copper complex catalyzed Diels-Alder reaction in ionic liquids: remarkable reactivity and selectivity enhancement, and efficient recycling of the catalyst |
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Authors: | Chang-Eun Yeom |
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Institution: | Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Republic of Korea |
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Abstract: | Ionic liquid was found to be an excellent medium for asymmetric Diels-Alder reaction catalyzed by chiral bis(oxazoline)-copper complex. The reactivity and selectivity of reactions were highly dependent upon the property of the ionic liquids. Reactions of β-substituted acryloyl dienophiles in Bmim]SbF6 at ambient temperature provided remarkably enhanced reactivity and stereoselectivity compared to homogeneous reactions in non-ionic liquid solvent at −78 °C. Due to the increased reactivity, the amount of metal catalyst could be reduced down to 0.6 mol % without any significant selectivity compromise. Additionally, recycling of the ligand-metal complex was achieved efficiently up to 18 times. |
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Keywords: | Asymmetric Diels-Alder Bis(oxazoline)-copper complex Ionic liquids Recycling Enantioselectivity |
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