Enantiomeric Recognition of Amino Acid Salts by Macrocyclic Crown Ethers Derived from Enantiomerically Pure 1,8,9,16-Tetrahydroxytetraphenylenes
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摘要Asymmetric 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.
著者Cheng C, Cai ZW, Peng XS, Wong HNC
期刊名稱Journal of Organic Chemistry
出版年份2013
月份9
日期6
卷號78
期次17
出版社AMER CHEMICAL SOC
頁次8562 - 8573
國際標準期刊號0022-3263
語言英式英語
Web of Science 學科類別Chemistry; Chemistry, Organic; CHEMISTRY, ORGANIC

上次更新時間 2020-22-10 於 01:31