Chiral C2-Symmetric Cu(II) Complex Immobilized in Ionic Liquids: A Recoverable Catalytic System for Enantioselective Hetero-Diels-Alder Reaction

Abstract Hydrophobic ionic liquids such as [Bmim]PF 6 and [Bmim]SbF 6 were used successfully as powerful media for bis(oxazoline)-copper-catalyzed asymmetric hetero-Diels-Alder reactions. The reactivities and stereoselectivities were comparable (ENDO/EXO up to 97:3 and up to 94% ee, respectively) to...

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Bibliographic Details
Published in:Synlett 2008-01, Vol.2008 (1), p.89-93
Main Authors: Shin, Yong Je, Yeom, Chang-Eun, Kim, Mi Jeong, Kim, B. Moon
Format: Article
Language:eng ; jpn
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Summary:Abstract Hydrophobic ionic liquids such as [Bmim]PF 6 and [Bmim]SbF 6 were used successfully as powerful media for bis(oxazoline)-copper-catalyzed asymmetric hetero-Diels-Alder reactions. The reactivities and stereoselectivities were comparable (ENDO/EXO up to 97:3 and up to 94% ee, respectively) to those of the corresponding homogeneous reactions. Furthermore, the reaction was remarkably accelerated in [Bmim]PF 6 compared to that in dichloromethane at 3 (±1) °C and metal-ligand complexes were recovered and recycled up to eight times exhibiting almost the same reactivity and selectivity.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2007-1000830