Jt-Allyl Palladium Reactions

As alluded to above, this version of the Jt-allyl palladium reaction uses an allylic acetate or chloride. The use of the acetate is more common because acetate is a much weaker nucleophile than chloride. When it involves a substrate where diastereomeric products can result, the stereochemistry of the nucleophilic displacement is an important issue. Palladium assisted alkylation proceeds with net retention of configuration of the acetate or chloride, as seen in the conversion of 375 to 376.223e,f... 

Since the Jt-allyl species is bound to palladium, there is a template effect in the Jt-allyl palladium reactions that can be exploited to form large rings (sec. 6.6.B).228 Ester 388 was converted to 389 in 70% yield by this procedure, but the yields have been poor in some cases.228... 

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