Alkylation of Allylic Derivatives. 9. On the Stereochemistry of Alkylation of Acyclic Allylic Alcohols by the Murahashi Method

Article abstract of DOI:10.1021/jo00210a007

The stereochemistry of alkylation of optically active trans-α-methyl-γ-phenylallyl alcohol (3-OH) by the Murahashi procdeure has been investigated.Alkylation with n-butyllithium results in almost exclusive syn γ-alkylation.With methyllithium, syn γ-alkylation also predominates.The syn stereochemistry in this acyclic system is opposite from that observed earlier in cyclic systems.Mechanistic implications of this reversal of stereochemistry are discussed.