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Catalytic Asymmetric Conjugate Addition/Oxidative Dearomatization Towards Multifunctional Spirocyclic Compounds

Authors

  • Dr. Alena Rudolph,

    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands), Fax: (+31) 50-363-4296
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  • Pieter H. Bos,

    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands), Fax: (+31) 50-363-4296
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  • Auke Meetsma,

    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands), Fax: (+31) 50-363-4296
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  • Prof. Dr. Adriaan J. Minnaard,

    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands), Fax: (+31) 50-363-4296
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  • Prof. Dr. Ben L. Feringa

    Corresponding author
    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands), Fax: (+31) 50-363-4296
    • Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands), Fax: (+31) 50-363-4296
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  • We thank T. D. Tiemersma-Wegman and M. J. Smith for technical support (HPLC and MS analysis) and Dr. T. den Hartog for useful discussions. Financial support from NWO-CW is gratefully acknowledged.

Abstract

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Naphthole mit einer α,β-ungesättigten Esterfunktion in der Seitenkette reagieren in einer CuI-katalysierten asymmetrischen konjugierten Addition mit anschließender CuII-vermittelter oxidativer Cyclisierung zu benzanellierten spirocyclischen Cyclohexenonen (siehe Schema). Dieses Eintopfverfahren führt zwei neue C-C-Bindungen und drei benachbarte Stereozentren ein und resultiert in hoch funktionalisierten Produkten.

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