Novel chiral stationary phases for optical resolution by ligand-exchange high-performance liquid chromatography

Direct separation of ?-hydroxy acid enantiomers by ligand exchange chromatography

“…The OH oxygen atom is cis-positioned with respect to the hydroxyproline nitrogen atom. C: The ternary complex structure suggested in Yuki et al 9 The amino group is cis-positioned with respect to the nitrogen atom of the selector molecule. plex is presented in Table 5.…”

Amino alcohol‐derived chiral stationary phases

“…65,66 Since then, the use of amino alcohols, including the (1S,2R)-norephedrine, has been reported for the preparation of CSPs to perform the CLEC. [69][70][71][72][73][74][75][76][77][78][79][80][81] The α-amino alcohol-based CSPs have been frequently reported in chiral separation without the use of the ligand exchange mode. 67,[82][83][84][85][86][87][88][89] First, Pirkle-type π-acidic CSP prepared by our group, based on an α-amino alcohol, was an (R)-phenylglycinol 3,5-dinitrobenzoyl derived CSP.…”

“…Studies using amino alcohols to prepare CSPs for chiral separations have been reported by Yuki et al, 70,71 Mamiany et al, 105 Hyun et al, 65,66,[72][73][74][75][76][77][78][79] and Ryoo et al 67,[73][74][75][76][77][82][83][84][85][86][87][88][89] The development of ligand-exchange CSPs based on amino alcohols and their derivatives was reviewed in 2018 based on the work of Hyun. 72 To the best of our knowledge, there have been no further studies on amino alcohol-based CSPs other than those mentioned above to this date.…”

Determination of the absolute stereochemistry of the fungal metabolite (R)-(−)-2-(4′-hydroxyphenyl)-2-hydroxyethanoic acid (pisolithin B)

“…Pisolithin B ( l a ) Pisolithin A (2a) and resolved by chiral stationary (8) and mobile (9) phase HPLC techniques, as well as by enzymatic methods (10). However, a facile approach to the synthesis of enantiomerically enriched samples is not yet available.…”