THE FIRST STEREOSELECTIVE PALLADIUM-CATALYZED CYCLOCARBONYLATION OF BETA,GAMMA-SUBSTITUTED ALLYLIC ALCOHOLS

beta,gamma-Substituted allylic alcohols react with CO in the presence of catalytic quantities of palladium acetate and 1,4-bis(diphenylphosp hino)butane affording alpha,beta-substituted-gamma-butyrolactones in 4 2-85% isolated yields. The complete stereoselectivity observed in some cases is a significant feature of the lactonization reaction, with (E )-allylic alcohols affording trans-disubstituted lactones. Depending o n the structure of the allylic alcohol used in the cyclocarbonylation reaction, the formation of the corresponding alkene or the beta,gamma- unsaturated carboxylic acid was observed as a side or the principal re action.