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Pd(0)-catalyzed amination in the synthesis of chiral derivatives of BINAM and their evaluation as fluorescent enantioselective detectors
Pure and Applied Chemistry ( IF 1.8 ) Pub Date : 2020-09-25 , DOI: 10.1515/pac-2020-0205
Alexei D. Averin 1, 2 , Olga K. Grigorova 1 , Anna S. Malysheva 1 , Alexander V. Shaferov 1 , Irina P. Beletskaya 1, 2
Affiliation  

Abstract A mini-review covers recent successes in the synthesis of (S)-1,1′-binaphthyl-2,2′-diamine (BINAM) using Pd(0)-catalyzed amination reactions. As a result, versatile compounds with C2-chiral backbone were synthesized, among them are derivatives bearing additional chiral amino and fluorophore groups like dansyl amide, 7-methoxycoumarin, 6-aminoquinoline, different macrocyclic compounds with oxadiamine and polyamine linkers were obtained as well. BINAM derivatives of various structures were evaluated as fluorescent enantioselective detectors for a series of model amino alcohols. Many of them were shown to be efficient in sensing certain enantiomers of the amino alcohols by selective changes in the emission in the presence of these analytes. Small changes in the structure of the BINAM derivatives lead to serious difference in the recognition ability of the compounds under investigation.

中文翻译:

Pd(0)-催化胺化合成 BINAM 手性衍生物及其作为荧光对映选择性检测器的评价

摘要 一篇小型综述涵盖了使用 Pd(0) 催化的胺化反应合成 (S)-1,1'-binaphthyl-2,2'-diamine (BINAM) 的最新成功。结果,合成了具有 C2-手性骨架的多功能化合物,其中包括带有额外手性氨基和荧光团的衍生物,如丹磺酰胺、7-甲氧基香豆素、6-氨基喹啉,还获得了具有氧二胺和多胺接头的不同大环化合物。各种结构的 BINAM 衍生物被评估为一系列模型氨基醇的荧光对映选择性检测器。通过在这些分析物存在下发射的选择性变化,它们中的许多被证明可以有效地检测氨基醇的某些对映异构体。
更新日期:2020-09-25
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