Transition Metal-Catalyzed [5 + 2] Cycloadditions of 2-Substituted-1-vinylcyclopropanes: Catalyst Control and Reversal of Regioselectivity

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Abstract

Studies on the stereo- and regioselectivity of rhodium(I)-catalyzed [5 + 2] cycloadditions of 2-substituted-1-vinylcyclopropanes are described. The relative stereochemistry of vicinal cyclopropane substituents is found to be conserved in these reactions, translating into distinct 1,4- or 1,5-stereorelationships in the cycloadducts. Exceptional regioselectivity in cyclopropane bond cleavage and even reversal of cleavage selectivity can be obtained through judicious selection of substituents and/or catalyst.

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