Bulletin of the Chemical Society of Japan p. 3423 - 3429 (1992)
Update date:2022-08-17
Topics:
Chen, Yun
Shiao, Ming-Tang
A monoamide derived from (-)-anti head-to-head coumarin dimer <(-)-CD> with propylamine has been successfully bonded to silica gel (Lichrospher 100 NH2: 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 NH2, followed by hydrolysis of the other lactone.CSP-1 and CSP-2 showed high enantioselectivity to trans-stilbene oxide with separation factors (α) at 2.42 and 2.46, respectively, and the (-)-isomer eluted first.The capacity factor (k') 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 CuSO4(aq), resolved DL-tryptophan, DL-tyrosine, and DL-phenylalanine (α = kD'/KL' = 1.14-1.33), which all contain aromatic chromophore.The stability difference of the ternary complexes formed with D-isomer and L-isomer is explained by steric hindrance and aromatic ?-? interactions.
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