Stereochemical aspects of intramolecular palladium catalysed [3+2] cycloadditions of methylenecyclopropanes

Article abstract of DOI:10.1016/0040-4020(96)00160-3

The preparation and intramolecular palladium catalysed [3+2] cycloaddition reactions of a range of substrates containing either stereochemically defined 2,3-disubstituted methylenecyclopropanes 3 or acrylate acceptors 12-15 are described. Evidence is presented which supports the hypothesis that these cycloaddition reactions proceed via palladium-trimethylenemethane type intermediates and that the two carbon-carbon bonds are formed in a highly asynchronous manner.