Identification of enantioselective extractants for chiral separation of amines and aminoalcohols

Chirality
Maartje SteensmaGerard J Kwant

Abstract

The major obstacle for the introduction of fractional reactive extraction as a chiral separation method in the chemical and pharmaceutical industries is the lack of versatile enantioselective extractants. Therefore, a rational approach is developed to transfer the extensive knowledge of chiral selectors reported in the literature on chiral recognition and other chiral separation techniques to extraction. Based on a similarity in separation mechanisms, it was expected that chiral selectors originating from a technique in which chiral recognition takes place in the liquid phase are most likely to function as enantioselective extractant. Using this approach, a selection of promising extractants was made from the literature and experimentally evaluated for the enantioseparation of aminoalcohols and amines. As a result, four enantioselective extractant systems, namely, dibutyl-L-tartrate with boric acid, N-(2-hydroxydodecyl)-L-hydroxyproline Cu(II) complex, N-dodecyl-L-hydroxyproline Cu(II) complex, and azophenolic crown ether, have been identified. The azophenolic crown ether system performed the best and demonstrated an enantioselectivity between 1.3-5.0 for five out of six test compounds. Identification of the enantioselective ex...Continue Reading

References

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Citations

Oct 19, 2006·Journal of Chromatography. a·Katarina BabićA B de Haan
Nov 26, 2010·Organic & Biomolecular Chemistry·Boelo SchuurBen L Feringa
Jan 29, 2010·Chemical Communications : Chem Comm·Bastiaan J V VerkuijlBen L Feringa
Jan 7, 2021·Nature Communications·Haofei HuangKwan Mook Kim
Jul 31, 2009·The Journal of Organic Chemistry·Bastiaan J V VerkuijlBen L Feringa

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