Separation of alkyne enantiomers by chiral column HPLC analysis of their cobalt-complexes

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Abstract

Separation of the enantiomers of new chiral alkynes in strategic syntheses and bioorthogonal studies is always problematic. The chiral column high-performance liquid chromatography (HPLC) method in general could not be directly used to resolve such substrates, since the differentiation of the alkyne segment with the other alkane/alkene segment is not significant in the stationary phase, and the alkyne group is not a good UV chromophore. Usually, a pre-column derivatization reaction with a tedious workup procedure is needed. Making use of easily-prepared stable alkyne-cobalt-complexes, we developed a simple and general method by analyzing the in situ generated cobalt-complex of chiral alkynes using chiral column HPLC. This new method is especially suitable for the alkynes without chromophores and other derivable groups.

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Liu, Q., Wang, J., Li, J., Wang, X., Lu, S., Li, X., … Gautier, A. (2017). Separation of alkyne enantiomers by chiral column HPLC analysis of their cobalt-complexes. Molecules, 22(3). https://doi.org/10.3390/molecules22030466

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