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    Pyridine containing chiral macrocycles: synthesis and their enantiomeric recognition for amino acid derivatives
    (Pergamon-Elsevier Science Ltd, 2011) Deniz, Pinar; Turgut, Yilmaz; Togrul, Mahmut; Hosgoren, Halil
    Four novel C(2)-symmetric enantiomerically pure, chiral pyridine-18-crown-6 type macrocycles containing lipophilic chains at the stereogenic centers were prepared. The enantioselectivity of the new ligands toward the enantiomers of D-,L-amino acid methyl ester derivatives were also determined by (1)H NMR titration method. These novel macrocycles have been showed to be strong complexing agents for D- and L-amino acid methyl ester hydrochloride salts (with K(ass) up to 13590 M(-1) and Delta G(0) up to 23.3 kJ mol(-1) and selectivity ratio: 80:20) by (1)H NMR titration methods. These macrocyclic hosts exhibited enantioselective binding towards the D-enantiomer of valine methyl ester hydrochloride with K(D)/K(L), up to 5.08 in CDCl(3) with 0.25% CD(3)OD. (C) 2011 Elsevier Ltd. All rights reserved.
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    Öğe
    Synthesis of C2-Symmetric Chiral Amino Alcohols: Their Usage as Organocatalysts for Enantioselective Opening of Epoxide Ring
    (Taylor & Francis Inc, 2010) Turgut, Yilmaz; Aral, Tarik; Karakaplan, Mehmet; Deniz, Pinar; Hosgoren, Halil
    A series of -amino alcohols derivatives were synthesized from (R)-2-amino-1-butanol and (S)-1,2-propanediol, and they have been used as organocatalaysts in the racemic ring opening of epoxide in good yields with high enantiomeric excess (up to 97%).