Synthesis of new chiral calix[4]azacrowns for enantiomeric recognition of carboxylic acids

Synthesis of Cyclic Calix-crown Derivatives and Using in the PhaseTransfer Reactions

“…To view the ion transport properties of these compounds liquid-liquid extraction studies were performed with alkali (Li + , Na b , Dedek, et al 1994Memon, et al, 2004;Qazi, et al 2013, Okur, et al, 2010 Bu metotlarda kullanılan adsorban veya ligantlar siklodekstrinler ve crown eterlerden sonra supramoleküler kimyada üçüncü bir bileşik olarak kabul edilen bir fenol formaldehit oligomeri olan "kaliksarenler'' dir. Kaliksarenler, kolaylıkla sentezlenebilmeleri ve farklı fonksiyonel gruplarla türevlendirilebilmeleri aynı zamanda katyon, anyon ve organik moleküllerle konuk-konak kompleksi oluşturabilmeleri sebebiyle son yıllarda çalışılan en önemli konulardan birisi haline gelmiştir (Karaküçük, et al 2005;Durmaz, 2007;Sayın, et al 2010;Sayın, et al 2013Yang, 2010Bereczki, 2006;Deligöz, et al 2008;Liu, et al 2009;Tabakcı, et al 2007;Bouhroum, et al 2008;Kim, et al 2003;Demirtaş, et al 2008;Memon, et al 2001;Creaven, et al 2006;Gao, et al 2007;Halouani, et al 2004;Ungaro, et al 2005;Chen, et al 2006;Alpoğuz, et al 2002;Uysal Akkus, et al 2008;Sayin, et al, 2011).…”

Application of L‐proline derivatives as chiral shift reagents for enantiomeric recognition of carboxylic acids

“…The investigation of the chiral recognition of carboxylic acids by artificial receptors was of critical importance in the preparation, separation, and analysis of enantiomerically pure carboxylic acids and disclosing the mechanism of interaction of the carboxylic acids with biological systems. Therefore, a variety of chiral shift reagents, such as chiral amines,19–24 amino alcohols,25 Tröger's Base,26 macrocyclic amines and amides,27–34 crown ethers,35–37 and calixarenes,38–43 have been described in the literature to determine the enantiomeric purity and understand the basis of the mechanism of host–guest complexations. To date, however, there are only a few examples of proline‐derived receptors44, 45 for the enantiomeric recognition of carboxylic acids.…”

Chiral calix[4]arenes bearing amino alcohol functionality as membrane carriers for transport of chiral amino acid methylesters and mandelic acid

“…Although many calixarene derivatives have been synthesized as membrane carriers for anions, 33 cations, 34,35 and neutral molecules, [36][37][38] only a few investigations 39 have been reported for chiral guests. Our recent studies in this field were mainly dedicated to synthesis of novel chiral receptors containing various functionalities including azacrown ethers, 40 aminonaphthol derivatives, 41,42 and amines 43 as well as their extraction abilities and enantiomeric recognition properties toward chiral carboxylic acids and amino acid derivatives, we herein report the synthesis of novel calix [4]arene derivatives bearing chiral amino alcohol moieties at the lower rim and their potential applications as carriers in transport of amino acids through bulk liquid membrane.…”