Simple access to 2-methylalk-2-enoates and insect pheromones by zinc-promoted reduction of Baylis-Hillman-derived allylic bromides

Tetrahedron

Volumn 60, Issue 44, 2004, Pages 9983-9989

  Fernandes, Luciano ^a   Bortoluzzi, Adailton J ^a   Sá, Marcus M ^a  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

2 Methylalkenoates; Baylis Hillman; Insect pheromones; Reduction; Trisubstituted olefins

Indexed keywords

BROMINE DERIVATIVE; ZINC DERIVATIVE;

ANALYTIC METHOD; ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL PROCEDURES; CHEMICAL REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

FORMICIDAE; INSECTA;

EID: 4644227926     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.08.018     Document Type: Article

References (63)

1. M.A. D'Auria, L. Minale, and R. Riccio Chem. Rev. 93 1993 1839 1895
2. A. Marfat, P.R. McGuirk, and P. Helquist J. Org. Chem. 44 1979 3888 3901
3. E.J. Corey, and X.-M. Cheng The Logic of Chemical Synthesis 1995 Wiley New York p 25
4. S. Nakatsu, A.T. Gubaidullin, V.A. Mamedov, and S. Tsuboi Tetrahedron 60 2004 2337 2349
5. J.M. Concellón, H. Rodríguez-Solla, and C. Méjica Tetrahedron Lett. 45 2004 2977 2979
6. S.E. Denmark, and J. Amburgey J. Am. Chem. Soc. 115 1993 10386 10387
7. H.C. Brown, and D. Basavaiah J. Org. Chem. 47 1982 5407 5409
8. D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811 891
9. Ciganek, E. Organic Reactions; Wiley: New York, 1997; Vol. 51, p 201.
10. S.E. Drewes, and N.D. Emslie J. Chem. Soc., Perkin Trans. 1 1982 2079 2083
11. W.R. Roush, and B.B. Brown J. Org. Chem. 58 1993 2151 2161
12. T. Jenn, and D. Heissler Tetrahedron 54 1998 97 106
13. D. Grassi, V. Lippuner, M. Aebi, J. Brunner, and A. Vasella J. Am. Chem. Soc. 119 1997 10992 10999
14. H.M.R. Hoffmann, and J. Rabe J. Org. Chem. 50 1985 3849 3859
15. A.M. Moiseenkov, B.A. Cheskis, N.A. Shpiro, G.A. Stashina, and V.M. Zhulin Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 39 1990 517 521
16. B.A. Cheskis, A.M. Moiseenkov, N.A. Shpiro, G.A. Stashina, and V.M. Zhulin Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 39 1990 716 720
17. C.R. Mateus, M.P. Feltrin, A.M. Costa, F. Coelho, and W.P. Almeida Tetrahedron 57 2001 6901 6908
18. D. Basavaiah, and R.S. Hyma Tetrahedron 52 1996 1253 1258
19. U. Shadakshari, and S.K. Nayak Tetrahedron 57 2001 4599 4602
20. D. Basavaiah, M. Krishnamacharyulu, R.S. Hyma, P.K.S. Sarma, and N. Kumaragurubaran J. Org. Chem. 64 1999 1197 1200
21. S. Ravichandran Synth. Commun. 31 2001 2055 2057
22. K. Pachamutu, and Y.D. Vankar Tetrahedron Lett. 39 1998 5439 5442
23. D. Basavaiah, and N. Kumaragurubaran Tetrahedron Lett. 42 2001 477 479
24. M. Hudlický Reductions in Organic Chemistry 1984 Wiley New York pp 62-69
25. M.G. Nascimento, S.P. Zanotto, S.P. Melegari, L. Fernandes, and M.M. Sá Tetrahedron: Asymmetry 14 2003 3111 3115
26. M.M. Sá J. Braz. Chem. Soc. 14 2003 1005 1010
27. J.M. Brand, R.M. Duffield, J.G. MacConnell, M.S. Blum, and H.M. Fales Science 179 1973 388 389
28. H.M.R. Hoffmann, and R. Buchholz Helv. Chim. Acta 74 1991 1213 1221
29. D. Basavaiah, P.K.S. Sarma, and A.K.D. Bhavani J. Chem. Soc., Chem. Commun. 1994 1091 1092
30. A.B. Charette, B. Côté, S. Monroc, and S. Prescott J. Org. Chem. 60 1995 6888 6894
31. C.E. Moppet, and J.K. Sutherland J. Chem. Soc. (C) 1968 3040 3042
32. L.M. Stephenson, R.V. Gemmer, and S.P. Current J. Org. Chem. 42 1977 212 214
33. E. LeGoff J. Org. Chem. 29 1964 2048 2050
34. F. Ameer, S.E. Drewes, R. Hoole, P.T. Kaye, and A.T. Pitchford J. Chem. Soc., Perkin Trans. 1 1985 2713 2717
35. L.A. Paquette, G.D. Bennett, M.B. Isaac, and A. Chhatriwalla J. Org. Chem. 63 1998 1836 1845
36. L.A. Paquette, and J. Méndez-Andino Tetrahedron Lett. 40 1999 4301 4304
37. T.-P. Loh, G.-Q. Cao, and J. Pei Tetrahedron Lett. 39 1998 1457 1460
38. A.G. González, M.H. Silva, J.I. Padrón, F. León, E. Reyes, M. Álvarez-Mon, J.P. Pivel, J. Quintana, F. Estévez, and J. Bermejo J. Med. Chem. 45 2002 2358 2361
39. Schlosser, M. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: New York, 1994; Chapter 1, pp 32-38.
40. J.A. Katzenellenbogen, and T. Utawanit J. Am. Chem. Soc. 96 1974 6153 6158
41. P.J. Kocienski, J.M. Ansell, and R.W. Ostrow J. Org. Chem. 41 1976 3625 3627
42. T. Mimura, Y. Kimura, and T. Nakai Chem. Lett. 1979 1361 1364
43. J.A. Miller, and G. Zweifel J. Am. Chem. Soc. 103 1981 6217 6219
44. N. Slougui, G. Rousseau, and J.-M. Conia Synthesis 1982 58 60
45. P. Coutrot, and A. Ghribi Synthesis 1986 790 792
46. R. Rossi, A. Carpita, and P. Cossi Tetrahedron 48 1992 8801 8824
47. S. Rafel, and J.W. Leahy J. Org. Chem. 62 1997 1521 1522
48. L. Hu, B. Liu, and C. Yu J. Org. Chem. 66 2001 5413 5418
49. Fernandes, L. Master's Dissertation, Departamento de Química, Universidade Federal de Santa Catarina (DQ/UFSC), Florianópolis, Brazil, 2003.
50. D. Basavaiah, A.J. Rao, and M. Krishnamacharyulu Arkivoc 7 2001 136 145
51. D. Basavaiah, M. Krishnamacharyulu, and A.J. Rao Synth. Commun. 30 2000 2061 2069
52. J. Cai, Z. Zhou, G. Zhao, and C. Tang Org. Lett. 4 2002 4723 4725
53. Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, 1984; Vol. 3, pp 111-118.
54. A.F. Hegarty, and F.L. Scott J. Am. Chem. Soc. 33 1968 753 762
55. Vogel A. I. Vogel's Textbook of Practical Organic Chemistry; Longman: New York, 5th ed.; 1989; p 467.
56. T. Naito, O. Miyata, T. Shinada, and I. Ninomiya Synthesis 1990 1123 1125
57. A.B. Smith III, J.L. Wood, A.E. Gould, S. Omura, and K. Komiyama Tetrahedron Lett. 32 1991 1627 1630
58. J.B. Stothers, and H. Brouwer Can. J. Chem. 50 1972 601 611
59. (a) Enraf-Nonius, CAD-4 EXPRESS Version 5.1/1.2; Enraf-Nonius, Delft, The Netherlands, 1994.
60. (b) Spek, A. L., HELENA -CAD-4 Data Reduction Program; University of Utrecht, The Netherlands, 1996.
61. A. Altomare, M.C. Burla, M. Camalli, G.L. Cascarano, C. Giacovazzo, A. Guagliardi, A.G.G. Moliterni, G. Polidori, and R. Spagna J. Appl. Cryst. 32 1999 115
62. (d) Sheldrick, G. M., SHELXL97, Program for the Refinement of Crystal Structures; University of Göttingen, Germany, 1997.
63. L.J. Farrugia J. Appl. Cryst. 30 1997 565