Hydrolytic kinetic resolution of epoxides catalyzed by chromium(III)-endo,endo-2,5-diaminonorbornane-salen [Cr(III)-DIANANE-salen] complexes.: Improved activity, low catalyst loading

被引：18

作者：

Berkessel, Albrecht ^{[1
]}

Ertuerk, Erkan ^{[1
]}

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 18期

关键词：

asymmetric catalysis; chromium; DIANANE-salen; epoxide opening; hydrolytic kinetic resolution;

D O I：

10.1002/adsc.200606181

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The hydrolytic kinetic resolution (HKR) of terminal epoxides, using chiral chromium(III)salen catalysts based on DIANANE (endo,endo-2,5-diaminonorbornane), was studied. A broad substrate scope was found for the chromium(III)-DIANANE catalysts, and very low loadings (down to 0.05 mol %) were needed to achieve high enantiomeric purities of both the remaining epoxides and the product diols (up to > 99% ee). Besides monosubstituted epoxides, 2-methyl-2-n-pentyloxirane, which is an example for 2,2-disubstituted epoxides, could be ring-opened in an asymmetric fashion with water in the presence of an electronically tuned chromium(III)-DIANANE complex.

引用

页码：2619 / 2625

页数：7

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