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Effects of ring substituents on enantioselective recognition of amino alcohols and acids in uryl-based binol receptors

Title
Effects of ring substituents on enantioselective recognition of amino alcohols and acids in uryl-based binol receptors
Authors
Nandhakumar R.Ryu J.Park H.Tang L.Choi S.Kim K.M.
Ewha Authors
김관묵
SCOPUS Author ID
김관묵scopus
Issue Date
2008
Journal Title
Tetrahedron
ISSN
0040-4020JCR Link
Citation
vol. 64, no. 33, pp. 7704 - 7708
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
The uryl-based binol aldehyde, (S)-2-hydroxy-2′-(3-phenyluryl-benzyl)-1,1′-binaphthyl-3-carboxaldehyde (1), binds 1,2-amino alcohols and amino acids stereoselectively by reversible formation of imine bond. Hydrogen bond (between uryl group and alcohol -OH moiety) plays an important role in the stereoselectivity of amino alcohols. Hence, any substituents on phenyl group in 1 are expected to affect H-bond ability of uryl group. To study the effects of ring substituents on the stereoselective recognition of amino alcohols, (substituted phenyl)uryl-based chiral binol receptors have been prepared. The receptors with electron-donating X substituents have been synthesized from (S)-2-methoxymethoxy-2′-hydroxy-1,1′-binaphthyl-3-carboxaldehyde and X-phenyluryl-benzyl bromide. The receptors with electron-withdrawing Y substituents, however, required a different synthetic strategy including transformation of an aldehyde to alcohol. The incorporation of the electron withdrawing groups slightly accelerated the stereoselective recognition property of the receptor. Though the acceleration is not so remarkable, this work demonstrates the versatile derivatization of 1 in achieving higher stereoselective recognition of 1,2-amino alcohols and stereoconversion of l-amino acids to d-amino acids. © 2008 Elsevier Ltd. All rights reserved.
DOI
10.1016/j.tet.2008.06.029
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자연과학대학 > 화학·나노과학전공 > Journal papers
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