Synthesis of ketene phenyl- and butyltelluroacetals by a Horner-Wittig route

Tetrahedron

Volumn 61, Issue 32, 2005, Pages 7712-7718

  Silveira, Claudio C ^a   Cella, Rodrigo ^a   Braga, Antonio L ^a   Jacob, Raquel G ^a   Lenardão, Eder J ^b   Perin, Gelson ^b  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b FEDERAL UNIVERSITY OF PELOTAS   (Brazil)

Author keywords

Aldehydes; Ketene telluroacetals; Tellurium and compounds; Wittig reaction

Indexed keywords

ACETAL DERIVATIVE; KETENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HORNER REACTION; HORNER WADSWORTH EMMONS REACTION; OLEFINATION; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 21844463307     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.05.085     Document Type: Article

References (59)

1. For reviews on preparation and reactivity of vinyl tellurides, see: (a) N. Petragnani, and H.A. Stefani Tetrahedron 61 2005 1613
2. M.L. Vieira, F.K. Zinn, and J.V. Comasseto J. Braz. Chem. Soc. 12 2001 586
3. R.E. Barrientos-Astigarraga, P. Castelani, J.V. Comasseto, H.B. Formiga, N.C. Silva, C.Y. Sumida, and M.L. Vieira J. Organomet. Chem. 623 2001 43
4. J.V. Comasseto, and R.E. Barrientos-Astigarraga Aldrichim. Acta 33 2000 66
5. J.V. Comasseto, L.W. Ling, N. Petragnani, and H.A. Stefani Synthesis 1997 373
6. N. Petragnani Best Synthetic Methods - Tellurium in Organic Synthesis 1994 Academic
7. Y.Z. Huang, and X.S. Mo Synlett 1998 93
8. X.S. Mo, and Y.Z. Huang Tetrahedron Lett. 36 1995 3539
9. M.J. Dabdoub, M.L. Begnini, T.M. Cassol, P.G. Guerrero Jr., and C.C. Silveira Tetrahedron Lett. 36 1995 7623
10. T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, and N. Sonoda Angew. Chem., Int. Ed. Engl. 26 1987 1187
11. S.M. Barros, J.V. Comasseto, and J.N. Berriel Tetrahedron Lett. 30 1989 7353
12. S.M. Barros, M.J. Dabdoub, V.B. Dabdoub, and J.V. Comasseto Organometallics 8 1989 1661
13. A. Ogawa, Y. Tsuboi, R. Obayashi, K. Yokoyama, I. Ryu, and N. Sonoda J. Org. Chem. 59 1994 1600
14. M.J. Dabdoub, and V.B. Dabdoub Tetrahedron 51 1995 9839
15. M.J. Dabdoub, R.G. Jacob, J.T.B. Ferreira, V.B. Dabdoub, and F.A. Marques Tetrahedron Lett. 40 1999 7159
16. M.J. Dabdoub, V.B. Dabdoub, and J.V. Comasseto Tetrahedron Lett. 33 1992 2261
17. M.J. Dabdoub, V.B. Dabdoub, P.G. Guerrero Jr., and C.C. Silveira Tetrahedron 53 1997 4199
18. Y.Z. Huang, and X.S. Mo Tetrahedron Lett. 39 1998 1945
19. T. Kanda, T. Sugiro, N. Kambe, and N. Sonoda Phosphorus Sulfur Silicon Relat. Elem. 67 1992 103
20. F.C. Tucci, A. Chieffi, J.V. Comasseto, and J.P. Marino J. Org. Chem. 61 1996 4975
21. J.V. Comasseto, and J. Berriel Synth. Commun. 20 1990 1681
22. D.N. Moraes, R.E. Barrientos-Astigarraga, P. Castelani, and J.V. Comasseto Tetrahedron 56 2000 3327
23. F.C. Tucci, A. Chieffi, and J.V. Comasseto Tetrahedron Lett. 33 1992 5721
24. M.A. Araujo, R.E. Barrientos-Astigarraga, R.M. Ellensohn, and J.V. Comasseto Tetrahedron Lett. 40 1999 5115
25. R.E. Barrientos-Astigarraga, D.N. Moraes, and J.V. Comasseto Tetrahedron Lett. 40 1999 265
26. J.P. Marino, F.C. Tucci, and J.V. Comasseto Synlett 1993 761
27. M.A. Araujo, and J.V. Comasseto Synlett 1995 1145
28. X. Huang, and C.Q. Zhao Synth. Commun. 27 1997 237
29. A. Chieffi, and J.V. Comasseto Tetrahedron Lett. 35 1995 4063
30. A. Chieffi, and J.V. Comasseto Synlett 1995 671
31. Y.Z. Huang, X.S. Mo, and L. Wang Tetrahedron Lett. 39 1998 419
32. M.J. Dabdoub, V.B. Dabdoub, and J.P. Marino Tetrahedron Lett. 41 2000 433
33. M.J. Dabdoub, V.B. Dabdoub, and J.P. Marino Tetrahedron Lett. 41 2000 437
34. J. Terao, N. Kambe, and N. Sonoda Tetrahedron Lett. 37 1996 4741
35. W.B. Jang, D.Y. Oh, and C.W. Lee Tetrahedron Lett. 41 2000 5103
36. Y. Nishibayashi, C.S. Cho, K. Ohe, and S. Uemura J. Organomet. Chem. 526 1996 335
37. G. Zeni, and J.V. Comasseto Tetrahedron Lett. 40 1999 4619
38. C.C. Silveira, A.L. Braga, A.S. Vieira, and G. Zeni J. Org. Chem. 68 2003 662
39. S. Uemura, S. Fukuzawa, and S.R. Patil J. Organomet. Chem. 243 1983 9
40. J. Gerard, and L. Hevesi Tetrahedron 57 2001 9109
41. X. Huang, and Y.P. Wang Tetrahedron Lett. 37 1996 7417
42. S. Uemura, and S.I. Fukuzawa Tetrahedron Lett. 23 1982 1181
43. For a review on Pd(II) catalyzed homo- and cross-coupling of vinyl tellurides, see: G. Zeni, A.L. Braga, and H.A. Stefani Acc. Chem. Res. 36 2003 731
44. S. Uemura, K. Ohe, J.R. Kim, K. Kudo, and N. Sugita J. Chem. Soc., Chem. Commun. 1985 271
45. K. Ohe, H. Takahashi, S. Uemura, and N. Sugita J. Organomet. Chem. 326 1987 35
46. K. Ohe, H. Takahashi, S. Uemura, and N. Sugita J. Org. Chem. 52 1987 4859
47. T. Kauffmann Angew. Chem., Int. Ed. Engl. 21 1982 410
48. G. Zeni, G. Perin, R. Cella, R.G. Jacob, A.L. Braga, C.C. Silveira, and H.A. Stefani Synlett 6 2002 975
49. J.W. Sung, C.P. Park, J.M. Gil, and D.Y. Oh J. Chem. Soc., Perkin Trans. 1 1997 591
50. M.J. Dabdoub, M.L. Begnini, and P.G. Guerrero Jr. Tetrahedron 54 1998 2371
51. P.J. Stang, K.A. Roberts, and L.E. Lynch J. Org. Chem. 49 1984 1653
52. C.C. Silveira, G. Perin, and A.L. Braga Tetrahedron Lett. 36 1995 7361
53. C.C. Silveira, G. Perin, A.L. Braga, and N. Petragnani Synlett 1995 58
54. C.C. Silveira, G. Perin, P. Boeck, A.L. Braga, and N. Petragnani J. Organomet. Chem. 584 1999 44
55. C.C. Silveira, G. Perin, A.L. Braga, M.J. Dabdoub, and R.G. Jacob Tetrahedron 55 1999 7421
56. C.C. Silveira, G. Perin, A.L. Braga, M.J. Dabdoub, and R.G. Jacob Tetrahedron 57 2001 5953
57. For a review on preparation of vinyl chalcogenides by Wittig and Horner-Wittig reactions, see: C.C. Silveira, G. Perin, R.G. Jacob, and A.L. Braga Phosphorus, Sulfur Silicon 172 2001 55
58. C.W. Lee, Y.J. Koh, and D.Y. Oh J. Chem. Soc., Perkin Trans. 1 1994 717
59. For a discussion regarding the steric factors see: M.S. Newman J. Am. Chem. Soc. 72 1950 4783