Palladium-catalyzed [3 + 2] intramolecular cycloaddition of alk-5-enylidenecyclopropanes.
Readily accessible alk-5-enylidenecyclopropanes undergo [3 + 2] intramolecular cycloaddition reactions upon treatment with appropriate palladium complexes. The method allows the rapid and efficient assembly of a variety of bicyclo[3.3.0]octane systems with up to three stereocenters. Preliminary theoretical calculations uncovered previously unsuspected mechanistic possibilities based on either a concerted pallada-ene-like rearrangement or a stepwise process involving zwitterionic intermediates.
Gulías
Moisés
M
Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, Spain.
García
Rebeca
R
Delgado
Alejandro
A
Castedo
Luis
L
Mascareñas
José L
JL