Fast and efficient preparation of Baylis-Hillman-derived (E)-allylic azides and related compounds in aqueous medium

Tetrahedron

Volumn 62, Issue 50, 2006, Pages 11652-11656

  Sá, Marcus M ^a   Ramos, Marcia D ^a   Fernandes, Luciano ^a  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

3,3 Sigmatropic rearrangement; Allylic azides; Allylic bromides; Aqueous solvents; Baylis Hillman reaction; Heterogeneous catalysis

Indexed keywords

ALLYL COMPOUND; AZIDE;

AQUEOUS SOLUTION; ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; ENVIRONMENT; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 33750609630     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.09.059     Document Type: Article

References (52)

1. Bräse S., Gil C., Knepper K., and Zimmermann V. Angew. Chem., Int. Ed. 44 (2005) 5188-5240
2. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 2596-2599
3. Scriven E.F.V., and Turnbull K. Chem. Rev. 88 (1988) 297-368
4. Hassner A. In: Scriven E.F.V. (Ed). Azides and Nitrenes (1984), Academic, New York, NY
5. Feldman A.K., Colasson B., Sharpless K.B., and Fokin V.V. J. Am. Chem. Soc. 127 (2005) 13444-13445
6. Mangelinckx S., Boeykens M., Vliegen M., Van der Eycken J., and De Kimpe N. Tetrahedron Lett. 46 (2005) 525-529
7. Cardillo G., Fabbroni S., Gentilucci L., Perciaccante R., Piccinelli F., and Tolomelli A. Org. Lett. 7 (2005) 533-536
8. Takasu H., Tsuji Y., Sajiki H., and Hirota K. Tetrahedron 61 (2005) 11027-11031
9. Khanetskyy B., Dallinger D., and Kappe C.O. J. Comb. Chem. 6 (2004) 884-892
10. Papeo G., Posteri H., Vianello P., and Varasi M. Synthesis (2004) 2886-2892
11. Trost B.M., and Pulley S.R. Tetrahedron Lett. 36 (1995) 8737-8740
12. Trost B.M., and Cook G.R. Tetrahedron Lett. 37 (1996) 7485-7488
13. Capaccio C.A.I., and Varela O. Tetrahedron: Asymmetry 11 (2000) 4945-4954
14. Cleophax J., Olesker A., Rolland A., Gero S.D., and Forchioni A. Tetrahedron 33 (1977) 1303-1308
15. Hu T., and Panek J.S. J. Am. Chem. Soc. 124 (2002) 11368-11378
16. Askin D., Angst C., and Danishefsky S.J. J. Org. Chem. 50 (1985) 5005-5007
17. Gagneux A., Winstein S., and Young W.G. J. Am. Chem. Soc. 82 (1960) 5956-5958
18. Fava C., Galeazzi R., Mobbili G., and Orena M. Tetrahedron: Asymmetry 12 (2001) 2731-2741
19. Kawabata H., Kubo S., and Hayashi M. Carbohydr. Res. 333 (2001) 153-158
20. Göksu S., Ozalp C., Seçen H., Sütbeyaz Y., and Saripinar E. Synthesis (2004) 2849-2854
21. Gagnon D., Lauzon S., Godbout C., and Spino C. Org. Lett. 7 (2005) 4769-4771
22. Sá M.M. J. Braz. Chem. Soc. 14 (2003) 1005-1010
23. Basavaiah D., Rao A.J., and Satyanarayana T. Chem. Rev. 103 (2003) 811-891
24. Ciganek E. Organic Reactions Vol. 51 (1997), Wiley, New York, NY pp 201-350
25. Foucaud A., and Guemmout F.E. Bull. Soc. Chim. Fr. (1989) 403-408
26. Nayak S.K., Thijs L., and Zwanenburg B. Tetrahedron Lett. 40 (1999) 981-984
27. Ko S.H., and Lee K.-J. J. Heterocycl. Chem. 41 (2004) 613-616
28. Sreedhar B., Reddy P.S., and Kumar N.S. Tetrahedron Lett. 47 (2006) 3055-3058
29. Chandrasekhar S., Basu D., and Rambabu Ch. Tetrahedron Lett. 47 (2006) 3059-3063
30. Patra A., Roy A.K., Batra S., and Bhaduri A.P. Synlett (2002) 1819-1822
31. Lubineau A., and Augé J. Topics in Current Chemistry Vol. 206 (1999), Springer, Berlin pp 2-40
32. Yadav J.S., Gupta M.K., Pandey S.K., Reddy B.V.S., and Sarma A.V.S. Tetrahedron Lett. 46 (2005) 2761-2763
33. Padwa A., and Sá M.M. Tetrahedron Lett. 38 (1997) 5087-5090
34. Padwa A., and Sá M.M. J. Braz. Chem. Soc. 10 (1999) 231-236
35. Fernandes L., Bortoluzzi A.J., and Sá M.M. Tetrahedron 60 (2004) 9983-9989
36. Nascimento M.G., Zanotto S.P., Melegari S.P., Fernandes L., and Sá M.M. Tetrahedron: Asymmetry 14 (2003) 3111-3115
37. Buchholz R., and Hoffmann H.M.R. Helv. Chim. Acta 74 (1991) 1213-1221
38. Das B., Banerjee J., and Ravindranath N. Tetrahedron 60 (2004) 8357-8361
39. Hoffmann H.M.R., and Rabe J. J. Org. Chem. 50 (1985) 3849-3859
40. Yadav J.S., Reddy B.V.S., and Madan C. New J. Chem. 25 (2001) 1114-1117
41. Foucaud A., and Gruiec A. New J. Chem. 15 (1991) 943-947
42. Chen H.-Y., Patkar L.N., Ueng S.-H., Lin C.-C., and Lee A.S.-Y. Synlett (2005) 2035-2038
43. Zvak V., Kovac J., Dandarova M., Gracza T., and Kriz M. Collect. Czech. Chem. Commun. 49 (1984) 1764-1773
44. Clark J.H. Green Chem. 8 (2006) 17-21
45. Sartori G., Ballini R., Bigi F., Bosica G., Maggi R., and Righi P. Chem. Rev. 104 (2004) 199-250
46. Breton G.W. J. Org. Chem. 62 (1997) 8952-8954
47. Bortoluzzi A.J., Fernandes L., and Sá M.M. Acta Crystallogr., Sect. E 62 (2006) o3391-o3392
48. Alvarez S.G., and Alvarez M.T. Synthesis (1997) 413-414
49. Cunha S. Quim. Nova 26 (2003) 948-951
50. Eagen M.C., and Cromwell N.H. J. Org. Chem. 39 (1974) 3863-3866
51. Lee K.Y., Gowrisankar S., Lee Y.J., and Kim J.N. Tetrahedron 62 (2006) 8798-8804
52. Basavaiah D., and Kumaragurubaran N. Tetrahedron Lett. 42 (2001) 477-479