Department of Chemistry
Enantiomeric recognition of amino acid salts by macrocyclic crown ethers derived from enantiomerically pure 1,8,9,16-Tetrahydroxytetraphenylenes
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 KL/KD = 4.1 and KD/KL = 3.9, respectively. The new chiral macrocyclic hosts would further enrich the host-guest chemistry. © 2013 American Chemical Society.
Source Publication Title
Journal of Organic Chemistry
American Chemical Society
Link to Publisher's Edition
Cheng, Chao, Zongwei Cai, Xiao-Shui Peng, and Henry N. C. Wong. "Enantiomeric recognition of amino acid salts by macrocyclic crown ethers derived from enantiomerically pure 1,8,9,16-Tetrahydroxytetraphenylenes." Journal of Organic Chemistry 78.17 (2013): 8562-8573.