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Electro‐Organic Stereoselective Dehydrogenative Homo‐Coupling of β‐Naphthylamines Derivatives
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-06-20 , DOI: 10.1002/ejoc.202400477
Maurizio Benaglia 1 , Simonetta Resta 2 , Fabrizio Medici 2 , Stefano Andolina 2 , Sergio Rossi 2
Affiliation  

the electrochemical stereoselective dehydrogenative homocoupling of b‐naphthylamine derivatives was investigated and successfully accomplished, the chiral diaryl amines being obtained in up to 60% yield. The use of an enantiopure b‐naphthylamine featuring an aminoalcohol as chiral auxiliary led to the expected 2,2’‐binaphthyl diamine derivative in up to 96/4 diastereoisomeric ratio. The application of the methodology to the intramolecular cross coupling of the enantiopure bis‐N‐β‐naphthylamine 1,2‐trans‐diamino cyclohexane led to the formation of a single enantiopure diastereoisomer in 37% yield.

中文翻译:


β-萘胺衍生物的有机电立体选择性脱氢均质偶联



研究并成功完成了 b-萘胺衍生物的电化学立体选择性脱氢自偶联,获得了高达 60% 的产率的手性二芳基胺。使用以氨基醇作为手性助剂的对映体纯 b-萘胺,得到了预期的 2,2'-联萘二胺衍生物,其非对映异构体比例高达 96/4。将该方法应用于对映纯双-N-β-萘胺1,2-反式-二氨基环己烷的分子内交叉偶联,形成单一对映纯非对映异构体,产率为 37%。
更新日期:2024-06-20
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