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Synthesis 2001; 2001(2): 0251-0261
DOI: 10.1055/s-2001-10808
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Conversion of Iodocyclopropanes into Cyclopropylzinc Chlorides and Pd(0)-Catalyzed Cross-Coupling of the Latter Derivatives with Alkenyl Iodides and Iodobenzene: Stereospecific Synthesis of 1,2-Bisalkenylcyclopropanes and 1-Alkenyl-2-phenylcyclopropanes

Edward Piers* , Philip D. G. Coish
  • *Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, V6T 1Z1 Canada; Fax +1(604)8222847; E-mail: epier§interchange.ubc.ca
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Publikationsdatum:
31. Dezember 2001 (online)

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A method for the preparation of functionalized cyclopropylzinc chlorides, which involves treatment of substituted 2-alkenyl-1-iodocyclopropanes with BuLi followed by transmetalation of the resultant cyclopropyllithium with zinc chloride, is described. Palladium(0)-catalyzed cross-coupling of the cyclopropylzinc chloride derivatives with alkenyl iodides or iodobenzene provides highly substituted 1,2-bisalkenylcyclopropanes or 1-alkenyl-2-phenylcyclopropanes. In two of the cases studied, the initially formed cis-1,2-bisalkenylcyclopropanes 27, 29 underwent partial Cope rearrangement under the cross-coupling conditions to afford the corresponding 1,4-cycloheptadienes 28 and 30, respectively.

palladium - cross-coupling - iodocyclopropanes - 1,2-bisalkenylcyclopropanes - rearrangements