The use of stabilized carbon nucleophiles in palladium(II)-catalyzed 1,4-oxidation of conjugated dienes

Article abstract of DOI:10.1016/S0040-4039(97)00674-6

Palladium(II)-catalyzed aerobic oxidation of conjugated dienes 3 having a stabilized carbon nucleophile in the side chain resulted in a carbocyclizalion with an overall 1,4-cis-addition to the diene. The reactions were carried under an atmosphere of molecular oxygen in DMSO. An interesting exolendo selectivity of the electron-withdrawing groups in the tether led to a control of the relative stereochemistry between four stereogenic centers.