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Synthesis of New Chiral Secondary 1,2-Diamines Based on Levopimaric Acid and Their Use as Ligands in Copper(II)-Catalyzed Asymmetric Henry Reaction
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2020-05-26 , DOI: 10.1134/s1070428020040077
V. N. Konev , Z. P. Pai , T. B. Khlebnikova

Abstract

Methods have been developed for the synthesis of new chiral imino amines and unsymmetrically substituted trans-1,2-diamines based on fumaropimaric acid. The new trans-1,2-diamines were tested as ligands in the copper(II)-catalyzed asymmetric Henry reaction of 4-nitrobenzaldehyde with nitromethane. The effect of substituents on the amino groups on the catalytic activity and asymmetric induction has been studied. The configuration of the major enantiomer has been found to be controlled by the size of substituents in the two amino groups of the ligand.


中文翻译:

基于左庚烷酸的新型手性仲1,2-二胺的合成及其在铜(II)催化的不对称亨利反应中的配体应用

摘要

已经开发了用于基于富马尿酸的新的手性亚氨基胺和不对称取代的反式-1,2-二胺的合成方法。在铜(II)催化的4-硝基苯甲醛与硝基甲烷的不对称亨利反应中,对新的反式-1,2-二胺作为配体进行了测试。研究了取代基对氨基的催化活性和不对称诱导的影响。已经发现主要对映体的构型受配体两个氨基中取代基的大小控制。
更新日期:2020-05-26
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