Palladium-catalyzed coupling reactions of thioimidate N-oxides: Access to α-alkenyl- And α-aryl-functionalized cyclic nitrones

Angewandte Chemie - International Edition

Volumn 49, Issue 3, 2010, Pages 577-580

  Schleiss, Julie ^a   Rollin, Patrick ^a   Tatiboüet, Arnaud ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

substituted nitrones; Coupling reactions; D ribose; Palladium; Synthetic methods

Indexed keywords

ALKENYL; CATALYZED COUPLING; COUPLING REACTION; CYCLIC NITRONES; D-RIBOSE; FUNCTIONALIZED; KETO-NITRONES; N-OXIDES; NITRONES; SYNTHETIC APPROACH; SYNTHETIC METHODS;

CHEMICAL REACTIONS;

PALLADIUM;

NITROGEN; NITROGEN OXIDE; NITRONES; OXIDE; PALLADIUM; SULFUR;

ARTICLE; BIOLOGICAL MODEL; CATALYSIS; CHEMISTRY; CYCLIZATION;

CATALYSIS; CYCLIZATION; MODELS, BIOLOGICAL; NITROGEN; NITROGEN OXIDES; OXIDES; PALLADIUM; SULFUR;

EID: 74549180642     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200905188     Document Type: Article

References (43)

1. R. A. Floyd, R. D. Kopke, C.-H. Choi, S. B. Foster, S. Doblas, R. A. Towner, Free Radical Biol. Med. 2008, 45, 1361-1374.
2. a) Y. Han, B. Tuccio, R. Lauricella, F. A. Villamena, J. Org. Chem. 2008, 73, 7108-7117;
3. b)F. A. Villamena, J. L. Zweier, Antioxid. Redox Signaling 2004, 6, 619-629;
4. c) C. E. Thomas, D. F. Ohlweiler, A. A. Carr, T. R. Nieduzak, D. A. Hay, G. Adams, R. Vaz, R. C. Bernotas, J. Biol. Chem. 1996, 277, 3097-3104.
5. a) R. C. F. Jones in Synthetic Applications of 1, 3-Dipolar Cycloaddition Chemistry Towards Heterocycles and Natural Products (Eds.: A. Padwa, W. H. Pearson), Wiley, New York, USA, 2002, Chapter!, pp. 1.-81;
6. b)J. Revuelta, S. Cicchi, A. Goti, A. Brandi, Synthesis 2007, 485-504, and references therein;
7. c) K. V. Luzyanin, A. G. Tskhovrebov, M. F. C. Guedes da Silva, M. Haukka, A. J. L. Pombeiro, V. Y. Kukushkin, Eur. J. Org. Chem. 2009, 5969-5978;
8. d)F.M. Cordero, M. Salvati, C. Vurchio, A. de Meijere, A. Brandi, J. Org. Chem. 2009, 74, 4225-4231;
9. e) E. Hýrošová, L. Fišera, M. Medvecký, H.-U Reissig, A. Al-Harrasi, M. Koóš, Arkivoc 2009, 9, 122-142;
10. f) S. Stecko, A. Mames, B. Furman, M. Chmielewski, J. Org. Chem. 2008, 73, 7402-7404;
11. g) S. Stecko, A. Mames, B. Furman, M. Chmielewski, J. Org. Chem. 2009, 74, 3094-3100;
12. h) M. Ueda, H. Miyabe, M. Teramachi, O. Miyata, T. Naito, J. Org. Chem. 2005, 70, 6653-6660.
13. a) E.-L. Tsou, S.-Y. Chen, M.-H. Yang, S.-C. Wang, T.-R. Rachel Cheng, W.-C. Cheng, Bioorg. Med. Chem. 2008, 76, 10198-10204;
14. b) J. M. Macdonald, H. T. Horsley, J. H. Ryan, S. Saubern, A.B. Holmes, Org. Lett. 2008, 70, 4227-4229;
15. c) P. Merino, I. Delso, T. Tejero, F. Cardona, M. Marradi, E. Faggi, C. Parmeggiani, A. Goti, Eur. J. Org. Chem. 2008, 2929-2947;
16. d) T. Ueda, M. Inada, I. Okamoto, N. Morita, O. Tamura, Org. Lett. 2008, 10, 2043-2046.
17. a) S. Desvergnes, Y. Vallée, S. Py, Org. Lett 2008, 10, 2967-2970;
18. b) K. P. Kaliappan, P. Das, Synlett 2008, 841-844;
19. c) V. Liautard, V. Desvergnes, O. R. Martin, Tetrahedron: Asymmetry 2008, 19, 1999-2002;
20. d) E. Racine, C. Bello, S. Gerber-Lemaire, P. Vogel, S. Py, J. Org. Chem. 2009, 74, 1766-1769;
21. e) E.-L. Tsou, Y.-T. Yeh, P-H. Liang, W.-C. Cheng, Tetrahedron 2009, 65, 93-100.
22. a) M. Gulla, L. Bierer, L. Redcliffe, S. Schmidt, V. Jäger, Arkivoc 2006, 7, 76-88;
23. b) I. A. Grigor'ev, Arkivoc 2009, 4, 136-154;
24. c) M. A. Voinov, T. G. Shevelev, T. V. Rybalova, Y. V. Gatilov, N. V. Pervukhina, A. B. Burdukov, I. A. Grigor'ev, Organometallics 2007, 26, 1607-1615.
25. D. Cerniauskaite, E. Gallienne, H. Karciauskaite, A. S. F. Farinha, J. Rousseau, S. Armand, A. Tatibouët, A. Sackus, P. Rollin, Tetrahedron Lett. 2009, 50, 3302-3305, and references therein.
26. J. W. Fahey, A. T. Zalcmann, P. Talalay, Phytochemistry 2001, 56, 5-51.
27. J. D. Hayes, M. O. Kelleher, I. M. Eggleston, Eur. J. Nutr. 2008, 47, 73-88.
28. Purified arylsulfatase (E.C.3.1.6.1) from Helix pomatia is currently used: a) EEC Regulation No. 1864/90, Enclosure VIII, Offic. J. Eur. Commun. 1990, L170, 27-34;
29. b)J.-P. Wathelet, R. Iori, O. Leoni, P. Rollin, A. Quinsac, S. Palmieri, Agroindustria 2004, 3, 257-266.
30. R. Iori, J. Barillari, E. Gallienne, C. Bilardo, A. Tatibouët, P. Rollin, Tetrahedron Lett. 2008, 49, 292-295.
31. R. M. Coates, S. J. Firsan, J. Org. Chem. 1986, 57, 5198-5209.
32. a) H. Prokopcová, C. O. C. Kappe, Angew. Chem. 2009, 121, 2312-2322;
33. Angew. Chem. Int. Ed. 2009, 48, 2276-2286;
34. b) D. A. Musaev, L. S. Liebeskind, Organometallics 2009, 28, 4639-4642;
35. c) S. Silva, S. Tardy, S. Routier, F. Suzenet, A. Tatibouët, A. P. Rauter, P. Rollin, Tetrahedron Lett 2008, 49, 5583-5586;
36. d) S. Silva, B. Sylla, F. Suzenet, A. Tatibouët, A. P. Rauter, P. Rollin, Org. Lett. 2008, 10, 853-856;
37. e) L. Pellegatti, E. Vedrenne, J.-M. Leger, C. Jarry, S. Routier, Synlett 2009, 2137-2142.
38. A. Chimiak, W. Przychodzen, J. Rachon, Heteroat Chem. 2002, 73, 169-194.
39. a) R. Grigg, M. Hadjisoteriou, P. Kennewell, J. Markandu, M. Thornton-Pett, J. Chem. Soc. Chem. Commun. 1992, 1388-1389;
40. b) R. Grigg, M. Hadjisoteriou, P. Kennewell, J. Markandu, M. Thornton-Pett, J. Chem. Soc. Chem. Commun. 1993, 1340-1343.
41. a) V. Jäger, L. Bierer, H.-Q. Dong, A. M. Palmer, D. Shaw, W. Frey, J. Heterocycl. Chem. 2000, 37, 455-465;
42. b)M. Gulla, L. Bierer, S. Schmidt, L. Redcliffe, V. Jäger, Z. Naturforsch. B. 2006, 61, 471-485.
43. N. Leconte, L. Pellegatti, A. Tatibouët, F. Suzenet, P. Rollin, G. Guillaumet, Synthesis 2007, 857-864.