TY - JOUR
T1 - Enantiomeric recognition of amino acid salts by macrocyclic crown ethers derived from enantiomerically pure 1,8,9,16-tetrahydroxytetraphenylenes
AU - Cheng, Chao
AU - CAI, Zongwei
AU - Peng, Xiao Shui
AU - Wong, Henry N.C.
N1 - Financial support from the Research Grants Council of the Hong Kong SAR, China (GRF Project 403909), an Area of Excellence Scheme established under the University Grants Committee of the Hong Kong SAR, China (Project No. AoE/ P-03/08), the Innovation and Technology Commission (Hong Kong) for the State Key Laboratory Scheme, the National Science Foundation of China (Grant No. 21272199), the Shenzhen Science and Technology Innovation Committee for the Municipal Key Laboratory Scheme, the Shenzhen Basic Research Program (JCY20120619151721025), and the CUHK Shenzhen Research Institute in the form of a start-up support fund is gratefully acknowledged.
PY - 2013/9/6
Y1 - 2013/9/6
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84883808171&partnerID=8YFLogxK
U2 - 10.1021/jo401240k
DO - 10.1021/jo401240k
M3 - Journal article
C2 - 23927033
AN - SCOPUS:84883808171
SN - 0022-3263
VL - 78
SP - 8562
EP - 8573
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 17
ER -