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
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
收藏
页码:776 / 783
页数:8
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