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Self-disproportionation of Enantiomers (SDE) of Chiral Nonracemic Amides via Achiral Chromatography |
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| Authors: | Alicja Wzorek Azusa Sato Józef Drabowicz Vadim A. Soloshonok |
| Affiliation: | 1. Institute of Chemistry, Jan Kochanowski University in Kielce, Świętokrzyska 15G, 25-406 Kielce, Poland;2. Department of Organic Chemistry I, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain Department of Chemistry, Tokyo Women's Medical University, 8-1 Kawada-cho, Shinjuku-ku, 162-8666 Tokyo, Japan;3. Department of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza112, 90-363 Łódź, Poland Institute of Chemistry, Environmental Protection and Biotechnology, Jan Długosz University in Częstochowa, Armii Krajowej 13/15, 42-201 Częstochowa, Poland;4. Department of Organic Chemistry I, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain |
| Abstract: | This article is based on a review of literature devoted to the phenomenon of SDE via achiral chromatography since the appearance of the seminal work of Professor Emanuel Gil-Av. The discussed examples of chromatographic studies are related to amides derived from chiral amines and α- and β-amino acids. We discuss the observed SDE magnitude as a function of a compound's structure, and composition of eluent and stationary phases, providing some mechanistic considerations. Particular emphasis is given to the aspect of SDE via achiral chromatography as an emerging unconventional enantiomeric purification technique. |
| Keywords: | achiral column chromatography amides amino acids homochiral and heterochiral molecular associations self-disproportionation of enantiomers (SDE) |