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

页码：8103 / 8110

页数：8

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