Enantioselective epoxidation of alkenes catalyzed by 2-fluoro-N-carbethoxytropinone and related tropinone derivatives

被引：64

作者：

Armstrong, A ^{[1
]}

Ahmed, G

Dominguez-Fernandez, B

Hayter, BR

Wailes, JS

机构：

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

[2] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 24期

关键词：

D O I：

10.1021/jo026322y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several alpha-substituted N-carbethoxytropinones have been evaluated as catalysts for asymmetric epoxidation of alkenes with Oxone, via a dioxirane intermediate. alpha-Fluoro-N-carbethoxytropinone (2) has been studied in detail and is an efficient catalyst which does not suffer from Baeyer-Villiger decomposition and can be used in relatively low loadings. This ketone was prepared in enantiomerically pure form using chiral base desymmetrization of N-carbethoxytropinone. Asymmetric epoxidation catalyzed by 2 affords epoxides with up to 83% ee. Among other derivatives tested, the alpha-acetoxy derivative 7 affords the highest enantioselectivities.

引用

页码：8610 / 8617

页数：8

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