A New Chirally Organized Trifluoromethylanthrylmethanol Derivative and Its Application as Chiral Solvating Agent

Abstract

The synthesis and structure of 1,1′‐(((10,10’‐(1,1′‐binaphthalene)‐2,2′‐diylbis(oxy))bis(methylene))bis(anthracene‐10,9‐diyl))bis(2,2,2‐trifluoroethanol), 4, is reported. This compound owns both axial and central chirality allowing its use as a chiral solvating agent (CSA) for the enantiomeric composition determination of several mixtures of chiral aromatic alcohols and amines using NMR. The study of the resulting diastereoisomeric complexes was carried out by determining its stoichiometry and association binding constants.

Efficient Enantiodifferentiation of Carboxylic Acids Using BINOL-Based Amino Alcohol as a Chiral NMR Solvating Agent

“…The chiral binaphthyl units and multiple hydrogen bonding sites containing hydroxyl, or amino groups, can provide an excellent candidate for chiral receptor sensors development (Yu and Pu, 2015;Pu, 2017), especially, they are broadly applicable CSA. For instance, commercially available (R)-or (S)-BINOL and derivatives as chiral-solvating agents to assign the enantiomeric excess (ee) of enantiomeric hydroxy carboxylic acids, synthetic drugs, natural alkaloids, or flavanones via 1 H NMR spectroscopy (Ardej-Jakubisiak and Kawecki, 2008;Freire et al, 2008;Klika et al, 2010;Redondo et al, 2010Redondo et al, , 2013Chaudhari and Suryaprakash, 2013;Mishra et al, 2014;Yuste et al, 2014;Borowiecki, 2015;Du et al, 2015;Yi et al, 2016;Monteagudo et al, 2017) and bifunctional BINOL-macrocycles containing diacylaminopyridine moieties were developed by Ema et al (2007Ema et al ( , 2008Ema et al ( , 2018; BINOL-derived disulfonimide extends the concept of CSA sensing to chiral recognition of O-heterocycles (Couffin et al, 2014); the crownophane and strapped calix[4]pyrrole containing built-in chiral BINOL were used for the enantioselective recognition of chiral amines and carboxylate anions, respectively (Tokuhisa et al, 2001;Miyaji et al, 2007). Chiral BINOL Brönsted acids were selected for determination of various indoloquinazoline alkaloid-type tertiary alcohols and various 3-arylquinazolinones (Liu et al, 2017;Wu et al, 2018), binaphthalene skeleton ureas as sensor for scanned various sulfoxides, phenylethanol, and arylpropanoic acids (Holakovský et al, 2015;Curínová et al, 2018Curínová et al, , 2019.…”