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

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• 作者：Bandini ; Marco ; Cozzi ; Pier Giorgio ; Umani-Ronchi ; Achille ; Villa ; Marzia
• 关键词：imines ; higher order cuprates ; zinc-copper reagents ; diastereoselection ; chiral amines
• 刊名：Tetrahedron
• 出版年：1999
• 出版时间：June 25, 1999
• 年：1999
• 卷：55
• 期：26
• 页码：8103-8110
• 全文大小：457 K

文摘

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.