Diastereoselective addition of higher order cuprates and zinc-copper reagents to imines derived from (S)-1-phenylethylamine
作者:Marco Bandini、Pier Giorgio Cozzi、Achille Umani-Ronchi、Marzia Villa
DOI:10.1016/s0040-4020(99)00418-4
日期:1999.6
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
考察了向(S)-1-苯基乙胺衍生的脂族和芳族手性亚胺的非对映选择性地添加了高阶(HO)铜酸盐和锌铜试剂。脂族的手性亚胺与(烯丙基)反应2 CuCNLi 2和(正丁基)2的Cu(CN)栗2在BF的存在3 ·的Et 2 O和我3的SiCl在高diastereoselection,而CC 6 ħ 11的Cu(CN ZnI和烯丙基Cu(CN)ZnBr可以在不添加添加剂的情况下以相当的收率得到手性胺。此外,据报道合成了针对δ-氨基酸的关键中间体。