Synthesis of Functionalized Cyclopentene Derivatives from Vinyldiazo Compounds and Vinylazides through Sequential Copper-Promoted [3+2] Cycloaddition/Azide Rearrangement

Abstract

The reaction of vinylazides with alkenyldiazo compounds in the presence of [Cu(CH3CN)4][BF4] provided cyclopentene derivatives retaining the azide functionality. This process would involve a sequence comprising: 1) decomposition of the diazo component with generation of a copper alkenylcarbene species; 2) stepwise regioselective [3+2] cycloaddition; 3) allylic azide rearrangement. A broad range of substrates is compatible with this protocol. We have also shown that azide-containing cycloadducts can be efficiently converted to the corresponding amine and triazole derivatives.