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Highly Enantioselective Organocatalytic Hydroxyalkylation of Indoles with Ethyl Trifluoropyruvate

Authors

  • Béla Török Prof. Dr.,

    1. Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA, Fax: (+1) 906-487-2061
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  • Mohammed Abid,

    1. Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA, Fax: (+1) 906-487-2061
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  • Gábor London,

    1. Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA, Fax: (+1) 906-487-2061
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  • Joseph Esquibel,

    1. Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA, Fax: (+1) 906-487-2061
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  • Marianna Török Dr.,

    1. Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA, Fax: (+1) 906-487-2061
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  • Shilpa C. Mhadgut,

    1. Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA, Fax: (+1) 906-487-2061
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  • Ping Yan Dr.,

    1. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661, USA, Fax: (+1) 213-740-6270
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  • G. K. Surya Prakash Prof. Dr.

    1. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661, USA, Fax: (+1) 213-740-6270
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  • Dedicated to Professor George A. Olah on the occasion of the 10th anniversary of his Nobel Prize. Financial support by the NSF (CHE-9512445) at Michigan Technological University and by the Loker Hydrocarbon Research Institute at USC is gratefully acknowledged. Professor Tse Lok Ho of National Chiao Tung University, Taiwan, is thanked for useful discussions.

Abstract

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Einfach verfügbare China-Alkaloide als Organokatalysatoren ermöglichten die hoch effiziente stereoselektive Hydroxyalkylierung von Heteroarenen wie den Indolen mit 3,3,3-Trifluorpyruvat (siehe Schema). Hohe Ausbeuten und ee-Werte beider Enantiomere der Produkte, je nach verwendetem Katalysator, belegen die Leistungsfähigkeit des Verfahrens.

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