Journal
TETRAHEDRON
Volume 61, Issue 33, Pages 7924-7930Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.06.014
Keywords
amino acid derivatives; macrocyclic hosts; enantioselectivity
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A series of new C-2-symmetric 2,2'-bipyridine-contaning crown macrocycles 1-4 has been developed for enantiomeric recognition of amino acid derivatives. These new macrocycles have been showed to be strong complexing agents for primary organic ammonium salts (with K up to 4.83 X 10(5) M-1 and -Delta G(0) up to 32.4 kJ mol(-1)) and also useful chromophores for UV-vis titration studies. These macrocyclic hosts exhibited enantioselective binding towards the (S)-enantiomer of phenylglycine methyl ester hydrochloride (Aml) with K-(S)/K-(R) up to 2. 10 (Delta Delta G(0) = - 1.84 kJ mol(-1)) in CH2Cl2 with 0.25% CH3OH. The structure-binding relationship studies showed that the aromatic subunit and the ester group of the ammonium guests are both important for good enantioselectivity. In addition, the host-guest complexes have been studied using various NMR experiments. (c) 2005 Elsevier Ltd. All rights reserved.
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