Synthesis of vinylphosphonates and its first exploration of bioactivity

Letters in Organic Chemistry

Volumn 8, Issue 6, 2011, Pages 416-422

  Li, Sheng Nan ^a   Xu, Lan Ting ^a   Chenb, Yue ^b   Lia, Ju Lian ^a   He, Ling ^a  

^a SICHUAN UNIVERSITY   (China)

^b SOUTHWEST MEDICAL UNIVERSITY   (China)

Author keywords

B nitro alkene; Phosphonation; Triethyl phosphite; Vinylphosphonate

Indexed keywords

EID: 79961093105     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017811796064467     Document Type: Article

References (38)

1. Ruiz, M.; Fernandez, M.C.; Diza, A.. Quintela, J.M. ; Ojea, V. Diastereoselective Synthesis of 2-Amino-4-phosphonobutanoic Acids by Conjugate Addition of Lithiated Schöllkopf's Bislactim Ethers to Vinylphosphonates. J.Org.Chem. 2003, 68, 7634-7645. (Pubitemid 37186114)
2. Fernández, M.C.; Quintela, J.M; Ruiz, M.; Ojea, M. Diastereoselective synthesis of 4-substituted 2-amino-4-phosphonobutanoic acids. Tetrahedron:Asymmetry. 2002, 13, 233-237 (Pubitemid 34261105)
3. Ruiz, M.; Fernández, M.C.; Conde, S.; Díaz, A.; Quintela, J.M.. Synthesis of 2-Amino-2-methyl-4-phosphonobutanoic Acids by Conjugate Addition of Lithiated Bislactim Ether Derived from Cyclo[Ala-d-Val] to Vinylphosphonates. Synlett. 1999, 12, 1903-1906.
4. Russell, J.A.; Ching, F.A.; Tashtoush, H.I.; Russell, J.E; Dedolph, D.F. Addition, substitution and deoxygenation reactions of .alpha.-phenyl-.beta.- nitrostyrenes with the anions of thiols and diethyl phosphite: formation of indoles by reaction with ethyl phosphates. J.Org.Chem. 1991, 56, 663-669.
5. Cheruku, P.; Paptchikhine, A.; Churchm, T.L.; Andersson. P.G.Iridium-N, P-Ligand-Catalyzed Enantioselective Hydrogenation of Diphenylvinylphosphine Oxides and Vinylphosphonates. J.Am.Chem.Soc.2009, 131, 8285-8289.
6. Wang, D.Y.; Hu, X.P.; Deng, J.; Yu, S.B.; Duan, Z.D.; Zheng, Z. Enantioselective Synthesis of Chiral α-Aryl or α-Alkyl Substituted Ethylphosphonates via Rh-Catalyzed Asymmetric Hydrogenation with a P-Stereogenic BoPhoz-Type Ligand. J.Org.Chem. 2009, 74, 4408-4410
7. Goulioukina, N.S.; Dolgina, T.M; Bondarenko, G.N.; Beletskaya, I.P.; Ilyin, M.M.; Davankov, V.A.; Pfaltz, A. Highly enantioselective hydrogenation of α, β-unsaturated phosphonates with iridium-phosphinooxazoline complex: synthesis of a phosphorus analogue of naproxen. Tetrahedron: Asymmetry. 2003, 14, 1397-1401. (Pubitemid 36859714)
8. Henry, J.C.; Lavergne, D.; Genet, J.P.; Beletskaya, I.P.; Dolgina, T.M. Asymmetric hydrogenation of vinylphosphonic acids and esters with chiral Ru(II) catalysts. Tetrahedron Lett.1998, 39, 3473-3476 (Pubitemid 28218301)
9. Gulyukina, N.S.; Varakuta, A.V.; Beletskaya, I.P. Synthesis of 1-arylcyclopropylphosphonates. Russ. Chem. Bull. 2007, 56, 1884-1890.
10. Batroff, V.; Flitsch, W.; Leaver, D.; Skinner, D. An improved Synthesis of Cyclazines from 3H-Pyrrolizines. Chem. Ber. 1984, 117, 1649-1658.
11. Finashina, E.D.; Isaeva, V.I.; Kustov, L.M.; Gulyukina, N.S.; Bondarenko, G.N. Catalytic synthesis of 1-arylethylphosphonates by the hydrogenation of unsaturated precursors in the presence of chitosan-based palladium catalysts. Russ. J. Org. Chem. 2006, 42, 990-995. (Pubitemid 44229687)
12. Barbara, B, ; Carlo, G.; Patrizia, G. Reactivity of Aryl and Vinyl Radicals: Abstraction of Hydrogen Atom or Reaction with a Nucleophile.Eur. J. Org. Chem. 2002, 16, 2844-2854.
13. Gulyukina, N.S.; Dolgina, T.M.; Bondarenko, G.N.; Beletskaya, I.P.; Bondarenko, N.A.; Henry, J.C.; Lavergne, D.; Ratovelomanana-Vidal, V.; Genet, J.P. Synthesis of Biologically Active 1-Arylethylphosphonates. Russ. J. Org. Chem. 2002, 38, 573-587. (Pubitemid 37116819)
14. In, S.C.; Howard, A.Reduction reactions using a binuclear palladium complex catalyst precursor and di-tert-butyl peroxide. J. Mol. Catal. A: Chem. 1996, 106, 7-10.
15. In, S.C.; Howard, A. Palladium Catalyzed Hydrogenation of .alpha., .beta.-Unsaturated Sulfones and Phosphonates. J. Org. Chem. 1994, 59, 4027-8
16. Xavier, C.; Cristina, C.G.; Kathryn, H. Mesylate derivatives of .alpha.-hydroxy phosphonates. Formation of carbocations adjacent to the diethyl phosphonate group. J. Am. Chem. Soc. 1983, 105, 2851-2858.
17. Gulyukina, N.S.; Dolgina, T.M.; Bondarenko, G. N.; Beletskaya, I. P. Russ. J. Org. Chem. 2003, 39, 797-807.
18. 2. J. Am. Chem. Soc .1996, 118, 1571-1572.
19. Goulioukina, N.S; Dolgina, T.M.; Beletskaya I.P.; Henry, J.C.; Lavergne, D.; Ratovelomanana-Vidal, V.; Genet, J.P. A practical synthetic approach to chiral α-aryl substituted ethylphosphonates. Tetrahedron: Asymmetry. 2001, 12, 319-327. (Pubitemid 32232207)
20. Glen, A. R.; Ching.F. Y. Reactions of ethyl phosphites with .beta.-nitrostyrenes. The role of nitrosoalkenes as intermediates. J. Org. Chem. 1992, 57, 6508-6513.
21. Glen, A. R.; Preecha, N. Substitution reactions in the .beta.-styryl and phenylethynyl systems. J. Org. Chem. 1989, 54, 1836-1842.
22. William, E.K.; Mary, B.M.; Anastasia, R.; John, R.M.; Behelfer, G.L.; Boland, B.E. Additions of trialkyl phosphites to nitroalkenes. J. Org. Chem. 1978, 43, 2877-2879.
23. Blicke, F.F.; Raines, S. The Preparation of Organic Phosphorus Compounds by Ivanov Reactions. II. J. Org. Chem. 1964, 29, 2036-2038.
24. Takeuchi, R.; Tsuji, Y.; Fujita, M.; Kondo, T.; Watanabe, Y.Platinum complex catalyzed carbonylation of organic iodides. Effective carbonylation of organic iodides having .beta.-hydrogens on saturated sp3 carbons. J. Org. Chem. 1989, 54, 1831-1836.
25. Pascal, A.T.W.P.; Ben, H.M.L.; Binne, Z. Synthesis and reactions of phosphoryl-substituted sulfines. J. Org. Chem. 1984, 49, 263-268.
26. George, A.; Surin, L; Robert, E. Reactions of copper(I) halide complexes of trivalent phosphorus with vinylic halides. J. Org. Chem. 1981, 46, 5200-5204.
27. Krawczyk, H.; Koszuk, J.; Bodalski, R. Pol. J. Chem. 2000, 74, 1123-1128.
28. He, L.; Yu, J.; Zhang, J.; Yu, X. -Q. α-Amidation of Cyclic Ethers Catalyzed by Simple Copper Salt and a Mild and Efficient Preparation Method for α, ω-Amino Alcohols. Org. Lett. 2007, 9, 2277.
29. Liang, J.-L.; Yuan, S.-X.; Huang, J.-S.; Che, C.-M. Intramolecular C..N Bond Formation Reactions Catalyzed by Ruthenium Porphyrins: Amidation of Sulfamate Esters and Aziridination of Unsaturated Sulfonamides. J. Org. Chem. 2004, 69, 3610-3619. (Pubitemid 38668217)
30. He, L.; Chan, P. W. H.; Tsui, W.-M.; Yu, W.-Y.; Che, C.-M. Ruthenium(II) Porphyrin-Catalyzed Amidation of Aromatic Heterocycles. Org. Lett. 2004, 6, 2405-2408. (Pubitemid 38952549)
31. Au, S.-M.; Huang, J.-S.; Yu, W.-Y.; Fung, W.-H.; Che, C.-M. Aziridination of Alkenes and Amidation of Alkanes by Bis(tosylimido)ruthenium(VI) Porphyrins. A Mechanistic Study. J. Am. Chem. Soc. 1999, 121, 9120.
32. Liang, J.-L.; Yuan, S.-X.; Huang, J.-S.; Yu, W.-Y.; Che, C.-M. Highly Diastereo- and Enantioselective Intramolecular Amidation of Saturated C=H Bonds Catalyzed by Ruthenium Porphyrins. Angew. Chem. Int. Ed. 2002, 41, 3465.
33. Müller, P.; Fruit, C. Enantioselective Catalytic Aziridinations and Asymmetric Nitrene Insertions into CH Bonds. Chem. Rev. 2003, 103, 2905.
34. Yang, J.; Weinberg, R.; Breslow, R. Enantioselective synthesis of tetrahydroisoquinolinesand benzazepines by silane terminated Heck reactions with the chiralligands (+)-TMBTP and (R)-BITIANP. Chem. Commun. 2000, 531.
35. Espino, C. G.; Du Bois, J. A Rh-Catalyzed C-H Insertion Reaction for the Oxidative Conversion of Carbamates to Oxazolidinones. Angew. Chem. Int. Ed. 2001, 40, 598.
36. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. Synthesis of 1, 3-Difunctionalized Amine Derivatives through Selective C-H Bond Oxidation. J. Am. Chem. Soc. 2001, 123, 6935.
37. Br3Cu(NCMe) . J. Am. Chem. Soc. 2003, 125, 12078.
38. Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Synthetic Studies toward the Guanacastepenes. Org. Lett. 2003, 5, 4113.