Further studies on sultones derived from carbene cyclization cycloaddition cascades

A sulfonyl-stabilized diazoketone underwent an efficient rhodium-catalyzed cascade reaction with an internal vinylsulfonate unit to give a tricyclic sultone as a single diastereomer. Nucleophilic addition of a vinyl Grignard reagent to the ketone of the resultant arylsulfonyl-substituted cycloadduct was stereocomplementary with respect to vinyl Grignard addition to corresponding ester-substituted substrates. The latter tricyclic compounds were chemoselectively transformed into vinylsultones via β-elimination in good yield.

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