Chirality Transfer in Palladium Catalyzed Reactions of Allylammonium Salts

Article abstract of DOI:10.1016/0957-4166(95)00021-G

Optically active 1-isobutyl-2(Z)-butenyltrimethylammonium iodide (10) underwent allylation with dimethyl sodiomalonate in the presence of a palladium(0) catalyst.The reaction proceeded predominantly with 1,3 transposition and with inversion of configuration, due probably to a prior isomerization from anti to syn-?-allylpalladium intermediate (14<*>15).The stereochemistry observed in the reaction with phenylzinc chloride was opposite to that with the soft nucleophile.