C-2-SYMMETRICAL BICYCLIC DIOLS AS CHIRAL LIGANDS IN THE TITANATE-CATALYZED ENANTIOSELECTIVE ADDITION OF ALKYLZINC REAGENTS TO ALDEHYDES

被引：42
|
作者：
WALDMANN, H [1 ]
WEIGERDING, M [1 ]
DREISBACH, C [1 ]
WANDREY, C [1 ]
机构：
[1] FORSCHUNGSZENTRUM JULICH, FORSCHUNGSZENTRUM, INST BIOTECHNOL, D-52425 JULICH, GERMANY
来源：
HELVETICA CHIMICA ACTA | 1994年 / 77卷 / 08期
关键词：
D O I：
10.1002/hlca.19940770803
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Enantiomerically pure C-2-symmetric 1,4-diols embodying bicyclic C-frameworks were synthesized by means of asymmetric carbo-Diels-Alder reactions as key steps (Scheme 1). They were investigated as chiral ligands in the enantioselective addition of ZnEt(2) to aromatic aldehydes. In the presence of 20-40 mol-% of the titanates formed from these diols and [Ti(i-PrO)(4)] at -78 degrees, the respective 1-arylpropanols were obtained with enantiomer ratios up to 93:7(Scheme 2, Table).
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页码：2111 / 2116
页数：6
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