Enhanced reactivity and enantioselectivity in catalytic glyoxylate-ene reactions using chiral bis(oxazoline)–copper complex in an ionic liquid |
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Authors: | Mina Kim Han Saem Jeong Chang-Eun Yeom B Moon Kim |
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Institution: | Department of Chemistry, College of Natural Sciences, Seoul National University, NS60, Seoul 151-747, South Korea |
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Abstract: | An optimal hydrophobic ionic liquid was discovered as a solvent for highly enantioselective glyoxylate-ene reactions catalyzed by a chiral bis(oxazoline)–copper complex. The reactivity and stereoselectivity were highly dependent upon the property of the ionic liquids; reactions between olefins and ethyl glyoxylate in Bmim]SbF6 at ambient temperature provided remarkably enhanced reactivity and stereoselectivity, which greatly exceed those of the corresponding reactions in dichloromethane. Furthermore, the metal–ligand complex was readily recycled up to eight times while exhibiting no significant decrease in reaction efficiency. |
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