Alkylation of Allylic Derivatives. 5. Loss of Double-Bond Configuration Associated with α-Alkylation of Allylic Carboxylates with Dialkylcuprates

Article abstract of DOI:10.1021/jo00153a020

Alkylation of cis- and trans-cinnamyl acetate with LiCuMe2 gives primarily the conjugated α-alkylation product, 1-phenyl-1-butene.Detectable loss of double-bond configuration is observed with the trans-acetate and substantial loss of configuration is observed with the cis-acetate.The partial loss of double-bond configuration in the α-alkylation product has profound mechanistic implications, which are discussed.