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Self-disproportionation of enantiomers of 3,3,3-trifluorolactic acid amides via sublimation |
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| Authors: | Manabu Yasumoto Vadim A. Soloshonok |
| Affiliation: | a Central Glass Co., 2805 Imafuku-nakadai Kawagoe, Saitama 350-1151, Japan b International Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), 1-1, Namiki, Tsukuba, Ibaraki 305-0044, Japan c Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of the Ukraine, Murmanska Street, Kyiv 94 02660, Ukraine d Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA |
| Abstract: | Preparation of racemic and enantiomerically enriched N-phenyl- and N-benzyl-3,3,3-trifluorolactic acid amides has been developed. These compounds were found to have substantial magnitude of the self-disproportionation of enantiomers (SDE) via sublimation. For example, when N-phenyl-3,3,3-trifluorolactic acid amide of 87% ee was sublimed (12 h) from a Petri dish at 80 °C open to the atmosphere, the enantiomeric excess of the remainder increased to 96% ee. On the other hand, when a sample of the same compound of 67% ee was subjected to SDE via sublimation under the same conditions, the enantiomeric excess has decreased to 18% ee. These preliminary results as well as excellent chemical and physico-chemical characteristics of these amide derivatives render them as readily available and very promising substrates for systematic study of SDE via sublimation. |
| Keywords: | Self-disproportionation of enantiomers (SDE) Enantiomeric enrichment/depletion Sublimation Evaporation Fluorine compounds |
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