Rh-catalyzed rearrangement of vinylcyclopropane to 1,3-diene units attached to N-heterocycles

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Abstract

Dienes embedded in quinolizidine and indolizidine structures can be prepared in four steps from cyclic nitrones and bicyclopropyl-idene. The key intermediates α-spirocyclopropanated N-heterocyclic ketones, generated via a domino 1,3-dipolar cycloaddition/thermal rearrangement sequence, were converted by Wittig methylenation to the corresponding vinylcyclopropanes (VCPs), which underwent rearrangement to 1,3-dienes in the presence of the Wilkinson Rh(I) complex under microwave heating. The previously unexplored Rh(I)-catalyzed opening of the VCP moiety embedded in an azapolycyclic system occurs at high temperature (110-130 °C) to afford the corresponding 1,3-dienes in moderate yield (34-53%).

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Cordero, F. M., Vurchio, C., Cicchi, S., De Meijere, A., & Brandi, A. (2011). Rh-catalyzed rearrangement of vinylcyclopropane to 1,3-diene units attached to N-heterocycles. Beilstein Journal of Organic Chemistry, 7, 298–303. https://doi.org/10.3762/bjoc.7.39

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