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
收藏
页码：4955 / 4957
页数：3
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