Selective Michael additions of primary and secondary amines to perfluoroalkylated sulfoxides and sulfones as a tool for fluorous tagging

Tetrahedron Letters

Volumn 47, Issue 51, 2006, Pages 9121-9124

  Magnier Bouvier, Caroline ^a   Blazejewski, Jean Claude ^b   Larpent, Chantal ^b   Magnier, Emmanuel ^b  

^a UMR 8233 CNRS Université Pierre et Marie Curie   (France)

^b UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

Aza Michael; Fluorous tags; Perfluoroalkyl chains; Sulfone; Sulfoxide

Indexed keywords

AMINE; BASE; REAGENT; SULFONE DERIVATIVE; SULFOXIDE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; MICHAEL ADDITION; PRECIPITATION; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION;

EID: 33750938701     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.077     Document Type: Article

References (51)

1. Selected references:. Kempe R. Angew. Chem., Int. Ed. 39 (2000) 468
2. Guiry P.J., McCarthy M., Lacey P.M., Saunders C.P., Kelly S., and Connolly D.J. Curr. Org. Chem. 4 (2000) 821
3. Ongeria S., Piarulli U., Rouxa M., Montia C., and Gennari C. Helv. Chim. Acta 85 (2002) 3388
4. Simpkins N.S. Tetrahedron 46 (1990) 6951
5. Simpkins N.S. In: Baldwin J.E., and Magnus P.D. (Eds). Sulfones in Organic Synthesis, Tetrahedron Organic Chemistry Series Vol. 10 (1993), Pergamon, Oxford
6. In: Patai S., Rappoport Z., and Stirling C.J. (Eds). The Chemistry of Functional Groups: The Chemistry of Sulfones and Sulfoxides (1998), Wiley, Chichester
7. Durst T. In: Barton D.H.R., and Ollis W.D. (Eds). Comprehensive Organic Chemistry (1979), Pergamon, Oxford pp 171-213
8. Enders D., Saint-Dizier A., Lannou M.-I., and Lenzen A. Eur. J. Org. Chem. (2006) 29 and references cited therein
9. Reddick J.J., Cheng J., and Roush W.R. Org. Lett. 5 (2003) 1967
10. Kahn S.D., and Hehre W.J. J. Am. Chem. Soc. 108 (1986) 7399
11. Lutolf M.P., and Hubbell J.A. Biomacromolecules 4 (2003) 713
12. Zhen G., Falconnet D., Kuennemann E., Vörös J., Spencer N.D., Textor M., and Zürcher S. Adv. Funct. Mater. 16 (2006) 243
13. Teyssot M.-L., Fayolle M., Philouze C., and Dupuy C. Eur. J. Org. Chem. (2003) 54
14. Pathak T. Eur. J. Org. Chem. (2004) 3361
15. For recent examples, see:. Indrajit D., Pathak T., and Suresh C. J. Org. Chem. 70 (2005) 8047
16. Mossé S., and Alexakis A. Org. Lett. 7 (2005) 4361
17. Enders D., Müller S.F., Raabe G., and Runsink J. Eur. J. Org. Chem. (2000) 879
18. Conjugate additions to trifluoromethylated acceptors:. Turconi J., Lebeau L., Paris J.-M., and Mioskowski C. Tetrahedron Lett. 47 (2006) 121 and references cited therein
19. Curran D.P., and Oderaotoshi Y. Tetrahedron 57 (2001) 5243
20. Koshti N., Reddy G.V., Jacobs H., and Gopalan A. Synth. Commun. 32 (2002) 3779
21. Goumont R., Magnier E., Kizilian E., and Terrier F. J. Org. Chem. 68 (2003) 6566
22. Bzhezovskii V.M., Il'chenko N.N., and Chura M.B. Russ. J. Gen. Chem. 76 (2006) 359
23. Bzhezovskii V.M., Chura M.B., and Il'chenko N.N. Russ. J. Gen. Chem. 76 (2006) 366
24. Amosova S.V., Gavrilova G.M., Albanov A.I., and Kalistratova E.F. Russ. J. Org. Chem. (Transl. Zh. Org. Khim.) 41 (2005) 1819
25. Amosova S.V., Gavrilova G.M., and Gostevskaya V.I. Russ. J. Org. Chem. (Transl. Zh. Org. Khim.) 37 (2001) 93
26. Knunyants I.L., Roshkov I.N., Aleksandrov A.M., and Yagupol'skii L.M. J. Gen. Chem. USSR (Engl. Transl.) 37 (1967) 1210
27. Haas A., and Popov V. J. Fluorine Chem. 20/1 (1982) 99
28. Abad E., Fayn J., Bertaina B., and Cambon A. J. Fluorine Chem. 24 (1984) 233
29. Magnier E., Tordeux M., Goumont R., Magder K., and Wakselman C. J. Fluorine Chem. 124/1 (2003) 55
30. Moïse J., Goumont R., Magnier E., and Wakselman C. Synthesis 14 (2004) 2297
31. Xu L.-W., Li J.-W., Xia C.-G., Zhou S.-L., and Hu X.-X. Synlett 15 (2003) 2425
32. Chaudhuri M.K., Hussain S., Kantam M.L., and Neelima B. Tetrahedron Lett. 46 (2005) 8329
33. For this experiment, dichloromethane is first saturated by gaseous ammonia and the Michael acceptor added. Ammonia is in excess, owing to its solubility in dichloromethane, accounting thus for the isolation of mono-adduct 11 as the sole reaction product. 11 is easily isolated by simple evaporation of the reaction mixture.
34. Cornils B. Angew. Chem., Int. Ed. 36 (1997) 2057
35. Curran D.P. Angew. Chem., Int. Ed. 37 (1998) 1174
36. Horváth I.T. Acc. Chem. Res. 31 (1998) 641
37. Fish R.H. Chem. Eur. J. (1999) 1677
38. De Wolf E., van Koten G., and Deelman B.-J. Chem. Soc. Rev. 28 (1999) 37
39. Kitazume T. J. Fluorine Chem. 105 (2000) 265
40. Dobbs A.P., and Kimberley M.R. J. Fluorine Chem. 118 (2002) 3
41. In: Gladysz J.A., Curran D.P., and Horváth I.T. (Eds). Handbook of Fluorous Chemistry (2004), Wiley-VCH, Weinheim, Germany
42. Sheldon R.A. Green Chem. 7 (2005) 267
43. Fache F. New J. Chem. 28 (2004) 1277
44. Hope E.G., and Stuart A.M. J. Fluorine Chem. 100 (1999) 75
45. Cavazzini M., Montanari F., Pozzi G., and Quid S. J. Fluorine Chem. 94 (1999) 183
46. Zang W. Chem. Rev. 104 (2004) 2531
47. Shepperson I., Quici S., Pozzi G., Nicoletti M., and O'Hagan D. Eur. J. Org. Chem. (2004) 4545
48. Agouridas V., Laïos I., Cleeren A., Kizilian E., Magnier E., Blazejewski J.-C., and Leclercq G. Bioorg. Med. Chem. 14 (2006) 7531
49. Zhang W., Chen C.H.-T., and Nagashima T. Tetrahedron Lett. 44 (2003) 2065-2068
50. Linclau B., Singh A.K., and Curran D.P. J. Org. Chem. 64 (1999) 2835
51. One of the referee is gratefully acknowledged for helpful comments.