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

被引：20
作者：
Bandini, M [1 ]
Cozzi, PG [1 ]
Umani-Ronchi, A [1 ]
Villa, M [1 ]
机构：
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
来源：
TETRAHEDRON | 1999年 / 55卷 / 26期
关键词：
imines; higher order cuprates; zinc-copper reagents; diastereoselection; chiral amines;
D O I：
10.1016/S0040-4020(99)00418-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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)(2)CuCNLi2 and (n-Bu)(2)Cu(CN)Li-2 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 delta-amino-acid was reported, (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：8103 / 8110
页数：8
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