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Urea- and Thiourea-Substituted Cinchona Alkaloid Derivatives as Highly Efficient Bifunctional Organocatalysts for the Asymmetric Addition of Malonate to Nitroalkenes: Inversion of Configuration at C9 Dramatically Improves Catalyst Performance.

Authors

  • Séamus H. McCooey,

    1. Centre for Synthesis and Chemical Biology, Department of Chemistry, Trinity College, University of Dublin, Dublin 2, Ireland, Fax: (+353) 1-671-2826
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  • Stephen J. Connon Dr.

    1. Centre for Synthesis and Chemical Biology, Department of Chemistry, Trinity College, University of Dublin, Dublin 2, Ireland, Fax: (+353) 1-671-2826
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  • Financial support from the Irish Research Council for Science Engineering and Technology is gratefully acknowledged. We would like to thank TopChem Laboratories Ltd. and the Gunnlaugsson group (TCD) for the use of their equipment.

Abstract

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Verkehrte Welt: Neuartige N-Aryl-Harnstoff- und N-Aryl-Thioharnstoffderivate von Dihydrocinchona-Alkaloiden katalysieren effizient die asymmetrische Addition von Dimethylmalonat an Nitroalkene. Die Aktivität und Selektivität der Katalysatoren hängt stark von der relativen Konfiguration an C8/C9 ab: Bereits in Konzentrationen von 0.5 Mol-% ergaben die Katalysatoren mit der „nichtnatürlichen“ Konfiguration an C9 hervorragende Aktivitäten und Enantioselektivitäten.

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