Enantiomeric Recognition of Amino Acid Salts by Macrocyclic Crown Ethers Derived from Enantiomerically Pure 1,8,9,16-Tetrahydroxytetraphenylenes
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AbstractAsymmetric synthesis of (R,R)- and (S,S)-1,8,9,16-tetrahydroxytetraphenylenes was achieved from starting material (2R,3R)-butane-2,3-diol and (2S,3S)-butane-2,3-diol respectively by utilizing a center-to-axis strategy. A series of crown ether compounds 20, 24, and 25 and their,corresponding enantiomers derived from chiral tetrahydroxytetraphenylene were synthesized in enantiomerically pure forms. Enantiomeric recognition properties of these hosts toward L- and D-amino acid methyl ester hydrochloride were studied by the UV spectroscopy titration. The tetramer hosts (S,S,S,S,S,S,S,S)-20 and (R,R,R,R,R,R,R,R)-20 exhibited the best enantioselectivities toward L- and D-alanine methyl ester hydrochloride salt with K-L/K-D = 4.1 and K-D/K-L = 3.9, respectively. The new chiral macrocyclic hosts would further enrich the host guest chemistry.
All Author(s) ListCheng C, Cai ZW, Peng XS, Wong HNC
Journal nameJournal of Organic Chemistry
Volume Number78
Issue Number17
Pages8562 - 8573
LanguagesEnglish-United Kingdom
Web of Science Subject CategoriesChemistry; Chemistry, Organic; CHEMISTRY, ORGANIC

Last updated on 2020-29-06 at 03:08