Alkylation of Allylic Derivatives. 3. The Regiochemistry of Alkylation of the Isomeric trans-α,γ-Methylphenylallyl Acetates with Lithium Dialkyleuprates

Article abstract of DOI:10.1021/jo00339a009

Alkylation of the isomeric trans-α,γ-methylphenylallyl acetates (1-OAc and 2-OAc) with lithium dimethylcuprate or di-n-butylcuprate is regioselective but not regiospecific.Both isomers give essentially the same product mixture which contains 95percent of the trans conjugated alkylation product (3).The starting acetates do not rearrange under the conditions for these reactions.These results show that the isomeric acetate give the same product-forming intermediate(s).Presumably the key intermediate that is common to the two isomers is a ?-allyl copper(III).