合成取代吗啉的新策略。
New strategy for the synthesis of substituted morpholines.
作者信息
Leathen Matthew L, Rosen Brandon R, Wolfe John P
机构信息
Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, USA.
出版信息
J Org Chem. 2009 Jul 17;74(14):5107-10. doi: 10.1021/jo9007223.
Abstract
A four-step synthesis of cis-3,5-disubstituted morpholines from enantiomerically pure amino alcohols is described. The key step in the synthesis is a Pd-catalyzed carboamination reaction between a substituted ethanolamine derivative and an aryl or alkenyl bromide. The morpholine products are generated as single stereoisomers in moderate to good yield. This strategy also provides access to fused bicyclic morpholines as well as 2,3- and 2,5-disubstituted products.
摘要
描述了一种从对映体纯的氨基醇出发，分四步合成顺式3,5-二取代吗啉的方法。该合成中的关键步骤是钯催化的取代乙醇胺衍生物与芳基或烯基溴之间的碳胺化反应。吗啉产物以单一立体异构体的形式生成，产率适中至良好。该策略还提供了获得稠合双环吗啉以及2,3-和2,5-二取代产物的途径。
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