Regioselective N-vinylation of cyclic thionocarbamates through a vinyl bis-sulfone methodology

Tetrahedron Letters

Volumn 45, Issue 34, 2004, Pages 6443-6446

  Girniene, Jolanta ^a,b   Tardy, Sébastien ^a   Tatibouët, Arnaud ^a   Sačkus, Algirdas ^b   Rollin, Patrick ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b KAUNAS UNIVERSITY OF TECHNOLOGY   (Lithuania)

Author keywords

BPSE; Carbohydrate; N Vinylation; Oxazinethione; Oxazolidinethione

Indexed keywords

CARBAMIC ACID DERIVATIVE; CARBOHYDRATE; NITROGEN DERIVATIVE; OXAZOLIDINE DERIVATIVE; SULFONE DERIVATIVE; THIOKETONE; VINYL DERIVATIVE;

ARTICLE; ATOM; CARBOHYDRATE ANALYSIS; METHODOLOGY; MICHAEL ADDITION; STEREOCHEMISTRY;

EID: 4143098025     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.124     Document Type: Article

References (37)

1. O. De Lucchi, V. Lucchini, L. Pasquato, and G. Modena J. Org. Chem. 49 1984 596 604
2. L. Pasquato, and O. De Lucchi L.A. Paquette Encyclopedia of Reagents for Organic Synthesis Vol. 1 1995 Wiley Chichester, UK 547
3. S. Cossu, O. De Lucchi, and P. Pasetto Angew. Chem., Int. Ed. 36 1997 1504 1506
4. S. Cossu, O. De Lucchi, P. Peluso, and R. Volpicelli Tetrahedron Lett. 40 1999 8705 8709
5. F. Chéry, P. Rollin, O. De Lucchi, and S. Cossu Tetrahedron Lett. 41 2000 2357 2360
6. F. Chéry, P. Rollin, O. De Lucchi, and S. Cossu Synthesis 2001 286 292 and references cited therein
7. E. Cabianca, F. Chéry, P. Rollin, S. Cossu, and O. De Lucchi Synlett 2001 1962 1964
8. E. Cabianca, F. Chéry, P. Rollin, A. Tatibouët, and O. De Lucchi Tetrahedron Lett. 43 2002 585 587
9. F. Chéry, M. Desroses, A. Tatibouët, O. De Lucchi, and P. Rollin Tetrahedron 59 2003 4563 4572
10. E. Cabianca, A. Tatibouët, F. Chéry, C. Pillard, O. De Lucchi, and P. Rollin Tetrahedron Lett. 44 2003 5723 5725
11. M. Desroses, F. Chéry, A. Tatibouët, O. De Lucchi, and P. Rollin Tetrahedron: Asymmetry 13 2002 2535 2539
12. W. He, K.E. Gonsalves, J.H. Pickett, and C. Halberstadt Biomacromolecules 4 2003 75 79
13. G. Theodoridis Tetrahedron Lett. 39 1998 9365 9368
14. P. Ciapetti, and M. Taddei Tetrahedron 54 1998 11305 11310
15. E. Abele, O. Dzenitis, K. Rubina, and E. Lukevics Chem. Heterocycl. Compd. 38 2002 682 685
16. D. Bogdal, and K. Jaskot Synth. Commun. 30 2000 3341 3352
17. H. Ishibashi, I. Kato, Y. Takeda, M. Kogure, and O. Tamura Chem. Commun. 2000 1527 1528
18. C. Gaulon, R. Dhal, and G. Dujardin Synthesis 2003 2269 2272
19. R. Dalpozzo, A. De Nino, L. Maiuolo, A. Procopio, R. Romeo, and G. Sindona Synthesis 2002 172 174
20. W. Reppe Liebigs Ann. Chem. 601 1956 81 104
21. C.K. Govindan Org. Process Res. Dev. 6 2002 74 77
22. A. Garcia, D. Rodriguez, L. Castedo, C. Saa, and D. Dominguez Tetrahedron Lett. 42 2001 1903 1905
23. R. Shen, and J.A. Porco Jr. Org. Lett. 2 2000 1333 1336
24. J.L. Brice, J.E. Meerdink, and S.S. Stahl Org. Lett. 6 2004 1845 1848
25. A. Fürstner, C. Brehm, and Y. Cancho-Grande Org. Lett. 3 2001 3955 3957
26. See for example: P. Daubos, V. Grumel, R. Iori, O. Leoni, S. Palmieri, and P. Rollin Ind. Crops Prod. 7 1998 187 193
27. O. Leoni, R. Bernardi, D. Gueyrard, P. Rollin, and S. Palmieri Tetrahedron: Asymmetry 10 1999 4775 4780 and references cited therein
28. D. Gueyrard, V. Grumel, O. Leoni, S. Palmieri, and P. Rollin Heterocycles 52 2000 827 843
29. D. Gueyrard, O. Leoni, S. Palmieri, and P. Rollin Tetrahedron: Asymmetry 12 2001 337 340
30. J. Girniene, D. Gueyrard, A. Tatibouët, A. Sackus, and P. Rollin Tetrahedron Lett. 42 2001 2977 2980
31. J. Girniene, A. Tatibouët, A. Sackus, J. Yang, G.D. Holman, and P. Rollin Carbohydr. Res. 338 2003 711 719
32. F. Fülöp, G. Csirinyi, and G. Bernath Synthesis 1985 1149 1151
33. O. Leoni, C. Marot, P. Rollin, and S. Palmieri Tetrahedron: Asymmetry 5 1994 1157 1160
34. J. Girniene, G. Apremont, A. Tatibouët, A. Sackus, and P. Rollin Tetrahedron 60 2004 2609 2619
35. S. Knapp, and A.T. Levorse J. Org. Chem. 53 1988 4006 4014
36. -1
37. -1