Highly enantioselective ring opening of cyclic meso-anhydrides to isopropyl hemiesters with Ti-TADDOLates:: An alternative to hydrolytic enzymes?

被引：70

作者：

Jaeschke, G ^{[1
]}

Seebach, D ^{[1
]}

机构：

[1] ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 04期

关键词：

D O I：

10.1021/jo971731t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Lewis acid mediated transfer of an alkoxide ligand from the chiral ligand sphere of Ti-TADDOLate (1) to cyclic meso anhydrides to afford the corresponding hemiesters is described. By using this method a variety of structurally different anhydrides can be converted to isopropyl hemiesters with high enantioselectivities (enantiomer ratios up to 99:1). We have also investigated Lewis acidic titanium complexes, which differ from 1 in the chiral ligand or the alkoxide ligand that is transferred. Finally, a catalytic version, which allows the substoichiometric use of Ti-TADDOLate in the presence of stoichiometric amounts of Al(Oi-Pr)(3), is presented.

引用

页码：1190 / 1197

页数：8

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