N-保护的2-环己烯-1-基胺的顺式和反式立体选择性环氧化反应
cis- and trans-stereoselective epoxidation of N-protected 2-cyclohexen-1-ylamines.
作者信息
O'Brien Peter, Childs Amanda C, Ensor Gareth J, Hill Cheryl L, Kirby Jonathan P, Dearden Michael J, Oxenford Sally J, Rosser Clare M
机构信息
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
出版信息
Org Lett. 2003 Dec 25;5(26):4955-7. doi: 10.1021/ol035873n.
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). [structure: see text]
关于N-保护的环状烯丙基胺在间氯过氧苯甲酸（m-CPBA）环氧化反应中的顺式和反式立体选择性的首次系统研究已经完成。单-N-保护体系生成具有顺式立体化学的环氧化物（酰胺作为顺式导向基团比磺酰胺或氨基甲酸酯更好），而双-N-保护体系生成反式环氧化物（对甲苯磺酰基-叔丁氧羰基（TsNBoc）保护给出完全的反式立体选择性）。[结构：见正文]
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