Regiocontrol and Stereoselectivity in Tungsten-Bipyridine Catalysed Allylic Alkylation

Article abstract of DOI:10.1016/0040-4020(95)00481-M

Tungsten-bipyridine complexes, generated in situ, catalyse the allylic alkylation of isocinnamyl methyl carbonate by dimethyl sodiomalonate with complete syn-stereoselectivity.When para substituted aryl-allyl methyl carbonates are employed, the regioselectivity correlates with Swain-Lupton parameters.Cross-over experiments demonstrate that the reactions do not proceed via the conventional 0> -> II allyl>⁺ -> 0 allyl-Nu> catalytic cycle.