cis- and trans-stereoselective epoxidation of N-protected 2-cyclohexen-1-ylamines

被引：54

作者：

O'Brien, P ^{[1
]}

Childs, AC ^{[1
]}

Ensor, GJ ^{[1
]}

Hill, CL ^{[1
]}

Kirby, JP ^{[1
]}

Dearden, MJ ^{[1
]}

Oxenford, SJ ^{[1
]}

Rosser, CM ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 26期

关键词：

D O I：

10.1021/ol035873n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The first systematic study of the cis and trans stereoselectivity in the m-CPBA epoxidation of N-protected cyclic allylic amines has been completed. Mono-N-protected systems gave epoxides with cis stereochemistry (amides are better cis directors than sulfonamides or carbamates) whereas di-N-protected systems gave trans-epoxides (TsNBoc protection gave complete trans stereoselectivity).

引用

页码：4955 / 4957

页数：3

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