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Nickel-Catalyzed Cyclizations of Enoates and Chiral Allenes: An Approach to Domoic Acid

Authors

  • Dr. Ahmad S. ElDouhaibi,

    1. Department of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, MI 48109-1055 (USA), Fax: (+1) 734-763-1106
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  • Dr. Refaie M. Kassab,

    1. Department of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, MI 48109-1055 (USA), Fax: (+1) 734-763-1106
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  • Dr. Minsoo Song,

    1. Department of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, MI 48109-1055 (USA), Fax: (+1) 734-763-1106
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  • Prof. Dr. John Montgomery

    Corresponding author
    1. Department of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, MI 48109-1055 (USA), Fax: (+1) 734-763-1106
    • Department of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, MI 48109-1055 (USA), Fax: (+1) 734-763-1106
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Abstract

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Come on allene, taloo-rye-aye! The first examples of nickel-catalyzed enoate/chiral allene cyclization reactions are reported. In the coupling process employing dimethylzinc, densely functionalized pyrrolidines are obtained with stereoselective installation of the C3 and C4 chiral centers and the diene functionality at C4. The process provides rapid access to an advanced intermediate towards the synthesis of domoic acid (see graphic).

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