Alkylation of Allylic Derivatives. 7. Stereochemistry of Alkylation of the Isomeric trans-α,γ-Methyl(phenyl)allyl Acetates with Lithium Dialkylcuprates and Alkylcyanocuprates

Article abstract of DOI:10.1021/jo00170a022

Alkylation of the isomeric trans-α,γ-methyl(phenyl)allyl acetates (2-OAc and 3-OAc) with lithium dialkylcuprates or alkylcyanocuprate is stereospecific.The α-alkylation product is formed with excess inversion, and the γ-alkylation product results from excess anti bonding.Stereospecificity ranges from about 85 to 95 percent in this sterically unbiased system.