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Enantioselective Recognition of Calix[4]arene Derivative Bearing Bicyclic Guanidinium for D/L Amino Acid Zwitterions
Author(s) -
Liu Fang,
Lu GuoYuan,
He WeiJiang,
Wang ZhenSheng,
Zhu LongGca
Publication year - 2001
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20010190321
Subject(s) - chemistry , bicyclic molecule , enantioselective synthesis , guanidine , calixarene , alkylation , derivative (finance) , stereochemistry , anhydrous , acetonitrile , medicinal chemistry , organic chemistry , molecule , catalysis , financial economics , economics
The p‐tetra ‐te r t‐butyl calix[4] arene derivatives (3 and 4) with (5,5) chiral bicyclic guanidinium, as the receptors of amino acid zwitterions, have been synthesized via a O‐alkylation reaction of p‐tetra ‐tert‐butyl calix [4] arene with cbJoromethyl chiral bicyclic guanidinium 2 in the presence of anhydrous K 2 CO 3 in acetonitrile. The results obtained from liquid‐liquid competitive extraction experiments indicate that the two receptors may selectively recognize L ‐aromatic amino acids, and that the enantioselective recognizability of the receptor 4 with two chiral bicyclic guanidinium units reachs up to about 90% for L‐Ph e.