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Organocatalytic stereoselective conjugate addition of 3-substituted oxindoles with in situ generated ortho-quinone methides
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2018-03-26 , DOI: 10.1016/j.tetlet.2018.03.069
Weihong Liang , Wenhao Yin , Tingzhong Wang , Fayang G. Qiu , Junling Zhao

A novel method for the stereoselective conjugate addition of 3-substituted oxindoles to in situ generated o-QMs was described. This process was catalyzed efficiently by a cinchonidine-derived squaramide catalyst in oil-water phase, furnishing the corresponding 3,3-disubsituted oxindole derivatives in moderate to high yields (up to 98%) with high stereoselectivities (up to 95% ee, 15.4:1 dr). The utility of this reaction was also investigated by the gram-scale synthesis and derivatization of one of the products.



中文翻译:

3-取代的羟吲哚与原位生成的醌甲基化物的有机催化立体选择性共轭加成

描述了一种将3-取代的羟吲哚立体选择性共轭加成到原位生成的o -QMs的新方法。该方法在油水相中由辛可尼定衍生的方酰胺催化剂有效地催化,以中等至高收率(高达98%)和高的立体选择性(高达95%ee,15.4)提供了相应的3,3-二取代的羟吲哚衍生物。 :1博士)。还通过克级合成和一种产物的衍生化研究了该反应的效用。

更新日期:2018-03-26
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