TY - JOUR
T1 - Enantioselective Complexation of Flexible and Rigid Substrates through Molecular Recognition
AU - Famulok, Michael
AU - Jeong, Kyu‐Sung ‐S
AU - Deslongchamps, Ghislain
AU - Rebek, Julius
PY - 1991/7
Y1 - 1991/7
N2 - Up to four hydrogen bonds are formed on complexation of hydantoins by 2,7‐naphthyl‐bridged dilactams. The L‐hydantoins (R may be CH2Ph, and CH(CH3)2, for example) bind preferentially to the (–)‐enantiomer of the receptor (ΔΔG = −0.6 kcal mol−1). Similarly, this enantioselectivity is observed in the complexation of L‐hydroorotic acid methyl ester. The selectivity of the binding of dipeptides, which are substantially more flexible, is less pronounced. (Figure Presented.)
AB - Up to four hydrogen bonds are formed on complexation of hydantoins by 2,7‐naphthyl‐bridged dilactams. The L‐hydantoins (R may be CH2Ph, and CH(CH3)2, for example) bind preferentially to the (–)‐enantiomer of the receptor (ΔΔG = −0.6 kcal mol−1). Similarly, this enantioselectivity is observed in the complexation of L‐hydroorotic acid methyl ester. The selectivity of the binding of dipeptides, which are substantially more flexible, is less pronounced. (Figure Presented.)
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U2 - 10.1002/anie.199108581
DO - 10.1002/anie.199108581
M3 - Article
AN - SCOPUS:33748241963
SN - 1433-7851
VL - 30
SP - 858
EP - 860
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 7
ER -