Design, preparation and performance of a phthalide-based chiral stationary phase
1987; Elsevier BV; Volume: 396; Linguagem: Inglês
10.1016/s0021-9673(01)94044-0
ISSN1873-3778
AutoresWilliam H. Pirkle, Thomas J. Sowin,
Tópico(s)Neuroscience and Neuropharmacology Research
ResumoA phthalide structurally optimized to maximize the chromatographic separability of its enantiomers on chiral stationary phases (CSPs) derived from the N-3,5-dinitrobenzamides of (S)-leucine and (R)-phenylglycine was prepared, preparatively resolved, and incorporated into a reciprocal phthalide-based CSP. This CSP, derived from 3-(4′,7′-dimethyl-1′-naphthyl)-3-(undec-10′-enyl) phthalide, has proven to be efficient for the separation of the enantiomers of numerous amino ester, amino amide, amino phosphonate, amino alcohol, amine, and alcohol 3,5-dinitrobenzoyl derivatives. Although not exhibiting the remarkably high degree of enantiomeric separation for some of the aforementioned analytes as some other reciprocal CSPs, the phthalide-based CSP is the most effective CSP to date for the separation of the enantiomers of secondary alcohols as their 3,5-dinitrobenzoates. Specific representative resolutions are presented for each of the aforementioned analyte classes. A study of the resolution of homologous series of α-phenylalkylamine and α-phenylalkanol derivatives is included.
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