Enantiodifferentiation of the antitumor alkaloid crispine A using the NMR chiral solvating agents (R)- and (S)-BINOL

Enantiodifferentiation of promethazine using (S)-(−)-BINOL as the NMR chiral solvating agent: determination of the enantiomeric purity and performance comparison with traditional chiral HPLC

“…Therefore, considering the results reported by Yuste et al 36 and the fact that (±)-1 is structurally related to a certain extent to (±)-crispine A (bearing a tertiary amine functional group) (Fig. 4), we decided to use the CSA-mediated NMR method to determine the enantiomeric purity of promethazine.…”

“…In addition, enantiomeric atropoisomers of BINOL exhibit a wide range of potential applications as CSA since they were reported to be suitable tools for the enantiomeric excess determination of a plethora of structurally different chiral compounds including sulfoxides, 30 sulfinimines, 31 thiosulfinates, 32 phytoalexins, 33 and various APIs such as fenfluramine, sertraline, and paroxetine 34 as well as montelukast, 35 crispine A, 36 and omeprazole and its analogues. 37 Several different BINOL derivatives have also been found to be effective chiral solvating agents toward a-hydroxy carboxylic acids, 38 amino acids, 39 and amines.…”

R-VAPOL-phosphoric acid based1H and13C-NMR for sensing of chiral amines and acids

“…13,[17][18][19] A number of chiral solvating agents are available in the literature such as macrocyclics, [20][21][22] metal complexes, 23 hydrogen bonding and ion-pair agents; 20,[24][25][26] some of which are synthetic and natural. [27][28][29][30][31][32][33][34] Recently, we have also made a signicant contribution in enantiodiscrimination and proposed various chiral solvating agents to the existing list of chiral auxiliary. 16,[35][36][37] Unfortunately, the use of single host chiral auxiliary is limited to a particular monofunctional group and therefore the enantiodiscrimination of polyfunctional group 13 requires various CSA depending on the sample of interest.…”

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.…”