Chromatographic optical resolution of acetylenylaziridines by HPLC on Chiralcel OD column

Abstract

The optical resolution of eleven acetylenylaziridines was examined by HPLC using tris(3,5-dimethylphenylcarbamate) of cellulose as the chiral stationary phase. Five aziridines having halogen, nitro and pyridinyl substituents on the aromatic ring were completely separated into enantiomers on Chiralcel OD with hexane/2-propanol mixture as an eluent. The results showed that the hydrogen bond, dipole-dipole and π-π interactions between dimethylphenylcarbamate group of Chiralcel OD and the polar groups of the aziridines may be responsible for the chiral recognition. This method had been applied to identify the optical purity of the products from asymmetric aziridination.

Key words: AZIRIDINE P, STATIONARY PHASE, CHIRALITY, MESOTOMY, ETHYNYL GROUP, HIGH SPEED LIQUID CHROMATOGRAPHY

CLC Number:

O621.16
O658

Cite this article

XIA LIJUN;LI ANHU;LIN LIN;DAI LIXIN. Chromatographic optical resolution of acetylenylaziridines by HPLC on Chiralcel OD column[J]. Chin. J. Org. Chem., 1997, 17(4): 381-384.

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乙炔基氮杂环丙烷类化合物在Chiralcel OD柱上的高效液相手性拆分