Chiral Stationary Phases Derived from (-)-anti Head-to-Head Coumarin Dimer: Preparation, Characterization, and Chiral Recognition Ability.
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A monoamide derived from (−)-<I>anti</I> head-to-head coumarin dimer [(−)-CD] with propylamine has been successfully bonded to silica gel (Lichrospher 100 NH<SUB>2</SUB>: Merck) through amide linkage to prepare CSP-1. Another monoamide derivative CSP-2 was prepared by direct nucleophilic opening of one lactone ring of (−)-CD by Lichospher 100 NH<SUB>2</SUB>, followed by hydrolysis of the other lactone. CSP-1 and CSP-2 showed high enantioselectivity to <I>trans</I>-stilbene oxide with separation factors (α) at 2.42 and 2.46, respectively, and the (−)-isomer eluted first. The capacity factor (<I>k</I>′) and α decrease with increasing polarity of the eluent (hexane/2-propanol), indicating that hydrogen bonding plays important role in chiral recognition. CSP-3, obtained by ligand exchange of CSP-2 with CuSO<SUB>4(aq)</SUB>, resolved <FONT SIZE="-2">DL</FONT>-tryptophan, <FONT SIZE="-2">DL</FONT>-tyrosine, and <FONT SIZE="-2">DL</FONT>-phenylalanine (α = <I>k</I><SUB>D</SUB>′/<I>k</I><SUB>L</SUB>′ = 1.14–1.33), which all contain aromatic chromophore. The stability difference of the ternary complexes formed with <FONT SIZE="-2">D</FONT>-isomer and <FONT SIZE="-2">L</FONT>-isomer is explained by steric hindrance and aromatic π-π interactions.
- 公益社団法人 日本化学会の論文
公益社団法人 日本化学会 | 論文
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