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Enantioselective organocatalytic α-sulfamidation of aldehydes using sulfonyl azides
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2017-10-27 , DOI: 10.1016/j.tetlet.2017.10.063
Raymond J. McGorry , Stacey K. Allen , Micha D. Pitzen , Thomas C. Coombs

Enantioselective organocatalytic α-sulfamidation of unbranched aldehydes is described using MacMillan’s second-generation imidazolidinone catalyst and o-nitrobenzenesulfonyl azide. The reactions are highly stereoselective (89.9–96.3% ee) with yields up to 71%. A strong correlation between aldehyde structure and product yield was found to exist, with 3-arylpropanals providing the best results. Application to functionalized amino acid synthesis is presented.



中文翻译:

磺酰叠氮化物对醛的对映选择性有机催化α-磺酰胺化

描述了使用麦克米兰的第二代咪唑烷酮催化剂和硝基苯磺酰基叠氮化物对非支链醛的对映选择性有机催化α-磺酰胺化反应。反应是高度立体选择性的(89.9–96.3%ee),产率高达71%。发现醛结构与产物产率之间存在强相关性,其中3-芳基丙醛提供最佳结果。介绍了在功能化氨基酸合成中的应用。

更新日期:2017-10-27
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