Mild and efficient one-pot synthesis of chiral β-chalcogen amides via 2-oxazoline ring-opening reaction mediated by indium metal

Journal of Organometallic Chemistry

Volumn 693, Issue 24, 2008, Pages 3563-3566

  Braga, Antonio L ^a   Galetto, Fábio Z ^a   Taube, Paulo S ^a   Paixão, Márcio W ^a,b   Silveira, Claudio C ^a   Singh, Devender ^a   Vargas, Fabrício ^a,b  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Chalcogen amides; 2 Oxazolines; Indium metal; Ring opening reaction

Indexed keywords

INDIUM; METALS; NITROGEN COMPOUNDS;

2-OXAZOLINES; CHALCOGEN; EFFICIENT; EXCELLENT YIELDS; ONE-POT; OPENING REACTIONS; OXAZOLINE RING; OXAZOLINES; RING-OPENING REACTION; STARTING MATERIALS; SYNTHESIS OF;

AMIDES;

EID: 54049141973     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.08.031     Document Type: Article

References (63)

1. For organoselenium compounds see:. Nicolaou K.C., and Petasis N.A. Selenium in Natural Products Synthesis (1984), CIS, Inc., Pennsylvania and references therein
2. Klayman D.L., and Günter W.H.H. Organoselenium Compounds: Their Chemistry and Biology (1973), Wiley, New York
3. Braga A.L., Reckziegel A., Silveira C.C., and Comasseto J.V. Synth. Commun. 24 (1994) 1165
4. For organosulfur compounds, see:. Dabbaka S.R., and Vogel P. Angew. Chem., Int. Ed. Engl. 44 (2005) 7674 and references therein
5. For selenium-containing chiral ligands, see:. Wirth T. Angew. Chem., Int. Ed. Engl. 39 (2000) 3740
6. Braga A.L., Lüdtke D.S., and Vargas F. Curr. Org. Chem. 10 (2006) 1921
7. Braga A.L., Lüdtke D.S., Vargas F., and Braga R.C. Synlett (2006) 1453
8. For sulfur-containing chiral ligands, see:. Anderson J.C., Cubbon R., Harding M., and James D.S. Tetrahedron: Asymmetr. 9 (1998) 3461
9. Mellah M., Voituriez A., and Schulz E. Chem. Rev. 107 (2007) 5133
10. Pellissier H. Tetrahedron 63 (2007) 1297
11. Braga A.L., Galetto F.Z., Rodrigues O.E.D., Silveira C.C., and Paixão M.W. Chirality 20 (2008) 839
12. Heppke G., Martens J., Praefcke K., and Simon H. Angew. Chem., Int. Ed. Engl. 16 (1977) 318
13. Cristiano R., Ely F., and Gallardo H. Liq. Cryst. 32 (2005) 15
14. Cristiano R., Westphal E., Bechtold I.H., Bortoluzzi A.J., and Gallardo H. Tetrahedron 63 (2007) 2851
15. Gamota D.R., Brazis P., Kalyanasundaram K., and Zhang J. Printed Organic and Molecular Electronics (2004), Kluwer Academic Publishers, New York
16. Balzani V., Credi A., M Raymo F., and Stoddart J.F. Angew. Chem., Int. Ed. 39 (2000) 3348
17. Woon K.L., Aldred M.P., Vlachos P., Mehl G.H., Stirner T., Kelly S.M., and O'Neill M. Chem. Mater. 18 (2006) 2311
18. Gallardo H., Zucco C., and Da Silva L. Mol. Cryst. Liq. Cryst. 373 (2002) 181
19. Yamada J., Akutsu H., Nishikawa H., and Kikuchi K. Chem. Rev. 104 (2004) 5057
20. Mugesh G., du Mont W.-W., and Sies H. Chem. Rev. 101 (2001) 2125
21. Nogueira C.W., Zeni G., and Rocha J.B.T. Chem. Rev. 104 (2004) 6255
22. Perottoni J., Rodrigues O.E.D., Paixão M.W., Zeni G., Lobato L.P., Braga A.L., Rocha J.B.T., and Emanuelli T. Food Chem. Toxicol. 42 (2004) 17
23. Braga A.L., Rodrigues O.E.D., Paixão M.W., Appelt H.R., Silveira C.C., and Bottega D.P. Synthesis (2002) 2338
24. Braga A.L., Paixão M.W., Lüdtke D.S., Silveira C.C., and Rodrigues O.E.D. Org. Lett. 5 (2003) 2635
25. Braga A.L., Silva S.J.N., Lüdtke D.S., Drekener R.L., Silveira C.C., Rocha J.B.T., and Wessjohann L.A. Tetrahedron Lett. 43 (2002) 7329
26. Braga A.L., Paixão M.W., and Marin G. Synlett (2005) 1975
27. Braga A.L., Lüdtke D.S., Sehnem J.A., and Alberto E.E. Tetrahedron 61 (2005) 11664
28. Santi C., and Wirth T. Tetrahedron: Asymmetr. 10 (1999) 1019
29. Wirth T. Tetrahedron Lett. 36 (1995) 7849
30. Sprinz J., Kiefer M., Helmchen G., Reggelin M., Huttner G., Walter O., and Zsolnai L. Tetrahedron Lett. 35 (1994) 1523
31. Zielinska-Blajet M., Siedlecka R., and Skarzewski J. Tetrahedron: Asymmetr. 18 (2007) 131
32. Andreadou I., Menge W.M.P.B., Commandeur J.N.M., Worthington E.A., and Vermeulen N.P.E. J. Med. Chem. 39 (1996) 2040
33. Sakakibara M., Katsumata K., Watanabe Y., Toru T., and Ueno Y. Synthesis (1992) 377
34. Bhasin K.K., Singh N., Kumar R., Deepali D.G., Metha S.K., Klapoetke T.M., and Crawford M.J. J. Organomet. Chem. 689 (2004) 3327
35. Crich D., and Grant D. J. Org. Chem. 70 (2005) 2384
36. do Rego Barros O.S., Lang E.S., de Oliveira C.A.F., Peppe C., and Zeni G. Tetrahedron Lett. 43 (2002) 7921
37. Peppe C., Lang E.S., Ledesma G.N., de Castro L.B., do Rego Barros O.S., and Mello P.D. Synlett (2005) 3091
38. Ranu B.C., and Das A. Adv. Synth. Catal. 347 (2005) 712
39. do Rego Barros O.S., de Carvalho A.B., Lang E.S., and Peppe C. Lett. Org. Chem. 1 (2004) 43
40. Braga A.L., Schneider P.H., Paixão M.W., Deobald A.M., Peppe C., and Bottega D.P. J. Org. Chem. 71 (2006) 4305
41. Ranu B.C., Mandal T., and Samanta S. Org. Lett. 5 (2003) 1439
42. Ranu B.C., and Mandal T. J. Org. Chem. 69 (2004) 5793
43. Ranu B.C. Eur. J. Org. Chem. (2000) 2343
44. Braga A.L., Schneider P.H., Paixão M.W., and Deobald A.M. Tetrahedron Lett. 47 (2006) 7195
45. Braga A.L., Vargas F., Galetto F.Z., Paixão M.W., Schwab R.S., and Taube P.S. Eur. J. Org. Chem. (2007) 5327
46. Braga A.L., Vargas F., Sehnem J.A., and Braga R.C. J. Org. Chem. 70 (2005) 9021
47. Vargas F., Sehnem J.A., Galetto F.Z., and Braga A.L. Tetrahedron 64 (2008) 392
48. Cintas P. Synlett (1995) 1087
49. Li C.-J. Tetrahedron 52 (1996) 5643
50. Li C.-J., and Chan T.H. Tetrahedron 55 (1999) 11149
51. Ranu B.C. Eur. J. Org. Chem. (2000) 2347
52. Jang D.O., and Cho D.H. Synlett (2002) 631
53. Munbunjong W., Lee E.H., Chavasiri W., and Jang D.O. Tetrahedron Lett. 46 (2005) 8769
54. Ueda M., Miyabe H., Nishimura A., Miyata O., Takemoto Y., and Naito T. Org. Lett. 5 (2003) 3835
55. Sugi M., Sakuma D., and Togo H. J. Org. Chem. 68 (2003) 7629
56. Miyabe H., Ueda M., Nishimura A., and Naito T. Org. Lett. 4 (2002) 131
57. Miyabe H., Nishimura A., Ueda M., and Naito T. Chem. Commun. (2002) 1454
58. Huang T., Keh C.C.K., and Li C.-J. Chem. Commun. (2002) 2440
59. Peppe C., and Tuck D.G. Can. J. Chem. 62 (1984) 2798
60. Hoveyda H.R., Karunaratne V., Rettig S.J., and Orvig C. Inorg. Chem. 31 (1992) 5408
61. Still W.C., Kahn M., and Mitra A. J. Org. Chem. 43 (1978) 2923
62. Gant T.G., and Meyers A.I. Tetrahedron 50 (1994) 2297
63. Braga A.L., Rubim R.M., Schrekker H.S., Wessjohann L.A., de Bolster M.W.G., Zeni G., and Sehnem J.A. Tetrahedron: Asymmetr. 14 (2003) 3291