Abstract
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) 2CuCNLi 2 and (n-Bu) 2Cu(CN)Li 2 in the presence of BF 3·Et 2O and Me 3SiCl in high diastereoselection, while c-C 6H 11Cu(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.
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