C-phosphorylated imines in synthesis of non-racemic α-fluoroalkylated aminophosphonic acid derivatives

References

• Ordóñez, M.; Rojas-Cabrera, H.; Cativiela, C. An Overview of Stereoselective Synthesis of α-Aminophosphonic Acids and Derivatives. Tetrahedron 2009, 65, 17–49. DOI: 10.1016/j.tet.2008.09.083.
   PubMed Web of Science ®Google Scholar
• (a) Rassukana Yu, V.; Kolotylo, M. V.; Sinitsa, O. A.; Pirozhenko, V. V.; Onys’ko, P. P. α-Iminotrifluoroethylphosphonates: The First Representatives of N-H Imidoyl Phosphonates. Synthesis 2007, 2007, 2627–2630. (b) Rassukana, Y. V.; Yelenich, I. P.; Synytsya, A. D.; Onys'ko, P. P. Fluorinated NH-Iminophosphonates and Iminocarboxylates: novel Synthones for the Preparation of Biorelevant α-Aminophosphonates and Carboxylates. Tetrahedron 2014, 70, 2928–2937. DOI: 10.1016/j.tet.2014.03.030. (c) Rassukana Yu, V.; Yelenich, I. P.; Bezdudny, A. V.; Mironov, V. F.; Onys’ko, P. P. Chemoselectivity of the Reactions of Haloacetonitriles with Hydrogen Phosphonates: The Dramatic Effect of the Nature of the Halogen Atom. Tetrahedron Lett. 2014, 55, 4771–4773.(d) Rassukana Yu, V.; Stanko, O. V.; Yelenich, I. P.; Onys'ko, P. P. Silylated Iminophosphonates: Novel Reactive Synthons for the Preparation of Fluorinated Aminophosphonates and Aminophosphonic Acids. Tetrahedron Lett. 2017, 58, 3449–3452.(e) Stanko, O. V.; Yelenich, I. P.; Onys’ko, P. P.; Rassukana Yu, V. NH-Polyfluoroalkyl Іminophosphonates in the Synthesis of α-Amino-α-Polyfluoroalkyl-γ-Oxobutylphosphonic Acids. J. Org. Pharm. Chem. 2019, 17, 5–10.
   Google Scholar
• Rassukana Yu, V.; Stanko, O. V.; Onys’ko, P. P. Enantiomeric O,O-Dimenthyl α-Iminotrifluoroethylphosphonates: novel Chiral Building Blocks in Asymmetric Synthesis of α-Trifluoromethylated α-Aminophosphonic Acid Derivatives. J. Fluorine Chem. 2019, 219, 123–128. DOI: 10.1016/j.jfluchem.2019.01.007.
   Web of Science ®Google Scholar
• Onys’ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D.; Kornilov, M. Y. Sigmatropic Isomerizations in Phosphorylated 2-Azaalyl Systems. VII. Asymmetric Induction in 1,3-H Shift in Diethyl 2,2,2-trifluoro-N-9(α-Methyl-Benzyl)Acetimidoyl Phosphonate. J. Gen. Chem. USSR (Engl. Transl.) 1990, 60, 1165–1168.
   Google Scholar
• Stanko, O. V.; Rassukana, Y. V.; Zamulko, K. A.; Dyakonenko, V. V.; Shishkina, S. V.; Onys’ko, P. P. Diastereoselective Synthesis of Polyfluoroalkylated α-Aminophosphonic Acid Derivatives. J. Fluorine Chem. 2018, 216, 47–56. DOI: 10.1016/j.jfluchem.2018.10.001.
   Web of Science ®Google Scholar
• Rassukana Yu, V.; Onys’ko, P. P.; Kolotylo, M. V.; Sinitsa, A. D.; Łyżwa, P.; Mikołajczyk, M. A New Strategy for Asymmetric Synthesis of Aminophosphonic Acid Derivatives: The First Enantioselective Catalytic Reduction of C-Phosphorylated Imines. Tetrahedron Lett. 2009, 50, 288–290. DOI: 10.1016/j.tetlet.2008.10.152.
   Web of Science ®Google Scholar
• Onys’ko, P. P.; Rassukana Yu, V.; Synytsya, O. A. Prototropic Isomerizations in the 2-Azaallylic Triad of Imidoylphosphonates. Curr. Org. Chem. 2010, 14, 1223–1233.
   Web of Science ®Google Scholar
• Onys’ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Sigmatropic Isomerizations in Azaallyl Systems: XXI. Alkaneimidoylphosphonates and Their Prototropic and Phosphorotropic Isomers. Russ. J. Gen. Chem. 2004, 74, 1868–1878. DOI: 10.1007/s11176-005-0110-8.
   Web of Science ®Google Scholar
• Rassukana, Y. V.; Bezgubenko, L. V.; Stanko, O. V.; Rusanov, E. B.; Kulik, I. B.; Onys'ko, P. P. Diastereoselective Cycloaddition of (S)-N-(1-Phenylethyl-Imino)Trifluoropropionate and Trifluoroethylphosphonate with Diazomethane. Tetrahedron: Asymmetry 2017, 28, 555–560. DOI: 10.1016/j.tetasy.2017.03.009.
   Google Scholar
• Rassukana Yu, V.; Bezgubenko, L. V.; Onys’ko, P. P.; Synytsya, A. D. Cycloaddition of (2-Organylimino)Trifluoropropionates with Diazomethane: Expedient Synthesis of 2-(Trifluoromethyl)Aziridine-2-Carboxylic Acids. J. Fluorine Chem. 2013, 148, 14–18. DOI: 10.1016/j.jfluchem.2013.01.019.
   Web of Science ®Google Scholar
• Rassukana Yu, V.; Yelenich, I. P.; Vlasenko, Y. G.; Onys’ko, P. P. Asymmetric Synthesis of Phosphonotrifluoroalanine Derivatives via Proline-Catalyzed Direct Enantioselective C–C Bond Formation Reactions of N–H Trifluoroacetimidoyl Phosphonate. Tetrahedron: Asymmetry 2014, 25, 1234–1238. DOI: 10.1016/j.tetasy.2014.07.007.
   Google Scholar
• Morisaki, K.; Sawa, M.; Yonesaki, R.; Morimoto, H.; Mashima, K.; Ohshima, T. Mechanistic Studies and Expansion of the Substrate Scope of Direct Enantioselective Alkynylation of α-Ketiminoesters Catalyzed by Adaptable (Phebox)Rhodium(III) Complexes. J. Am. Chem. Soc. 2016, 138, 6194–6203.
   PubMed Web of Science ®Google Scholar
• Stanko, O. V.; Rassukana Yu, V.; Onys’ko, P. P. Fluorinated Iminophosphonates Bearing Stereodirecting Phenylethyl Group in Synthesis of Biorelevant Scalemic Aminophosphonates. Phosphorus, Sulfur. Silicon Relat. Elem. 2019, 194, 325–326.
   Web of Science ®Google Scholar