Enantiomeric Recognition of Amino Acid Salts by Macrocyclic Crown Ethers Derived from Enantiomerically Pure 1,8,9,16-Tetrahydroxytetraphenylenes

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• 作者：Chao Cheng ; Zongwei Cai ; Xiao-Shui Peng ; Henry N. C. Wong
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：September 6, 2013
• 年：2013
• 卷：78
• 期：17
• 页码：8562-8573
• 全文大小：695K
• 年卷期：v.78,no.17(September 6, 2013)
• ISSN：1520-6904

文摘

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鈥揼uest chemistry.