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A Catalytic Asymmetric Three-Component 1,4-Addition/Aldol Reaction: Enantioselective Synthesis of the Spirocyclic System of Vannusal A

Authors

  • K. C. Nicolaou Prof. Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858–784–2469
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
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  • Wenjun Tang Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858–784–2469
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
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  • Philippe Dagneau,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858–784–2469
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
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  • Raffaella Faraoni Dr.

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858–784–2469
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
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  • We thank Dr. D. H. Huang and Dr. G. Siuzdak for NMR spectroscopic and mass spectrometric assistance, respectively. Financial support for this work was provided by grants from the National Institutes of Health (USA) and the Skaggs Institute for Chemical Biology, and a fellowship from the Swiss National Science Foundation (to R.F.).

Abstract

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Drei sind nicht immer ein Auflauf: Eine Dreikomponentenreaktion zwischen α,β-ungesättigten Enonen 1, Aldehyden 2 und Alkenylzirconiumverbindungen 3 in Gegenwart eines Rh-binap-Katalysators führt nacheinander in guten Ausbeuten und mit hohen ee-Werten zu Aldolen 4, Enonen 5 und 2,3-disubstituierten Cycloalkanonen 6.

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