Diastereoselective addition of higher order cuprates and zinc-copper reagents to imines derived from (S)-1-phenylethylamine

Article abstract of DOI:10.1016/S0040-4020(99)00418-4

The diastereoselective addition of higher order (H.O.) cuprates and zinc-copper reagents to aliphatic and aromatic chiral imines derived from (S)-1-phenylethylamine was examined. Aliphatic chiral imines react with (Allyl)₂CuCNLi₂ and (n-Bu)₂Cu(CN)Li₂ in the presence of BF₃-Et₂O and Me₃SiCl in high diastereoselection, while c-C₆H₁₁Cu(CN)ZnI and AllylCu(CN)ZnBr afford chiral amines in comparable yields without additives. Moreover the synthesis of a key intermediate towards a δ-amino-acid was reported.