Asymmetric Synthesis Using Chiral Acetals : Highly Diastereoselective Addition of Organocerium Reagents to Chiral α-Aldoxime-Ether Acetal

Nucleophilic addition of organometallic reagents [organocerium reagents (RMgX-CeCl3, RLi-CeCl3), Grignard reagent, and organolithium reagents] to the chiral α-aldoxime-ether acetal (1) was studied.Among the reagents, organocerium reagents showed higher reactivity and stereoselectivity, giving the N-oxygenated chiral amine derivatives (6Aa-c) in a highly diastereoselective manner, whereas Grignard and organolithium reagents afforded no 6.As an application of the reaction, the synthesis of (-)-N-acetylamphetamine (11) was achieved.