DIASTEREOSELECTIVITY IN IODOTRIMETHYLSILANE-PROMOTED CONJUGATE ADDITIONS OF ORGANOCOPPER REAGENTS TO CHIRAL ALPHA,BETA-UNSATURATED IMIDES AND AMIDES

被引：25

作者：

BERGDAHL, M ^{[1
]}

ILIEFSKI, T ^{[1
]}

NILSSON, M ^{[1
]}

OLSSON, T ^{[1
]}

机构：

[1] CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 18期

关键词：

D O I：

10.1016/0040-4039(95)00336-B

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conjugate additions of MeCu, PhCu and BuCu to the chiral enoylimides 2 a-c in the presence of iodotrimethylsilane and lithium iodide in THF give the adducts, 4a-c in yields above 90% and diastereoselectivities from 80 to 93%. The dominating diastereomers are different from those formed with LiR(2)Cu/TMSCl or in copper(I)-mediated addition of Grignard reagents. Corresponding additions to enoylamides of O-tritylprolinol also give high yields of conjugate adducts, but lower diasrereoselectivities, with dominating configuration in the acyl part opposite to those from the imides.

引用

页码：3227 / 3230

页数：4

共 17 条

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