Highly enantioselective conjugate addition of AlMe3 to linear aliphatic enones by a designed catalyst

被引：89

作者：

Fraser, PK ^{[1
]}

Woodward, S ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2003年 / 9卷 / 03期

关键词：

alanes; asymmetric catalysis; cuprates; S ligands; thioethers;

D O I：

10.1002/chem.200390087

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2-Hydroxy-2'-alkylthio-1,1'-binaphthyl compounds are catalytic promoters of the 1,4-addition of AlMe3 to linear aliphatic enones in THF at -40 to -48degreesC in the presence of [Cu(MeCN)(4)]BF4. At ligand loadings of 5-20 mol %, enantioselectivities of 80 - 93 % are realised for most substrates. To attain these values, the use of highly pure AlMe3 is mandatory. The presence of methylalumoxane (MAO), derived by hydrolysis, leads to reduced enantioselectivity and a conjugate addition product.

引用

页码：776 / 783

页数：8

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