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Highly Enantioselective Synthesis of 1,2,3-Substituted Cyclopropanes by Using α-Iodo- and α-Chloromethylzinc Carbenoids

Authors

  • Louis-Philippe B. Beaulieu,

    1. Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, H3C 3J7 (Canada), Fax: (+1) 514-343-7586
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  • Dr. Lucie E. Zimmer,

    1. Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, H3C 3J7 (Canada), Fax: (+1) 514-343-7586
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  • Prof. Alexandre Gagnon,

    1. Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, H3C 3J7 (Canada), Fax: (+1) 514-343-7586
    2. Department of Chemistry, Université du Québec à Montréal, P.O. Box 8888, Succ. Centre-Ville, Montréal, H3C 3P8 (Canada)
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  • Prof. André B. Charette

    Corresponding author
    1. Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, H3C 3J7 (Canada), Fax: (+1) 514-343-7586
    • Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, H3C 3J7 (Canada), Fax: (+1) 514-343-7586
    Search for more papers by this author

Abstract

Herein, we report the enantio- and diastereoselective formation of trans-iodo- and trans-chlorocyclopropanes from α-iodo- and α-chlorozinc carbenoids by using a dioxaborolane-derived chiral ligand. The synthetically useful iodocyclopropane building blocks were derivatized by an electrophilic trapping of the corresponding cyclopropyl lithium species or a Negishi coupling to give access to a variety of enantioenriched 1,2,3-substituted cyclopropanes. The synthetic utility of this method was demonstrated by the formal synthesis of an HIV-1 protease inhibitor. In addition, the related stereoselective bromocyclopropanation was also investigated. New insights about the relative electrophilicity of haloiodomethylzinc carbenoids are also presented.

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