Phthalimides reaction with allylic esters

The reaction of 2-pyrimidone with vinyl epoxide 16 also takes place under neutral conditions, as oxidative addition of 16 to palladium(O) generates an alkoxide that is sufficiently basic to deprotonate 2-pyrimidone22. In contrast, allyl ester (lS,4/ )-18 demands the use of the potassium phthalimide salt for C-N bond formation33. Similar to the purine /V-allylations with 16 and 18, only the depicted isomers 26 and (15,4f )-27 result. Potassium phthalimide thus represents another ammonia equivalent in palladium(0)-catalyzed allylic substitutions66. 

The nickel-catalyzed synthesis of Z-allylic alcohols in a two-step, one-pot reaction from conjugated dienes has been reported (Scheme 2.3) [4]. The key with this chemistry was the initial hydroboration of the 1,3-diene promoted by common nickel catalysts. Once the intermediate allylboronate was formed, treatment with NaOH/H Oj provided the alcohols. This chemistry was an attractive route to allylic alcohols as a range of functional groups including preexisting primary alcohols, esters, ethers, and phthalimides were well tolerated. 

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