PALLADIUM-CATALYZED REACTION OF NUCLEOPHILES WITH DIACETATES OF ALLYLIC 1,1-DIOLS

Article abstract of DOI:10.1016/0022-328X(84)80246-6

The reactions of allylic 1,1-diol diacetates (I) with carboanions under the catalysis of Pd(PPh3)4 were studied.Sodium diethyl malonate reacted with I to form an abnormal product resulting from the attack of the diethyl malonate carboanion on the carbonyl carbon of the acetoxy group, while sodium diethyl acetylmalonate gave the normal reaction products with high regioselectivity.The mechanisms of these reactions are discussed.