Ring opening of heterocycles by an arene-catalyzed lithiation

Pure and Applied Chemistry

Volumn 75, Issue 10, 2003, Pages 1453-1475

  Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; LITHIUM; NAPHTHALENE; NITROGEN; OXYGEN; POLYCYCLIC AROMATIC HYDROCARBON; SULFUR;

CATALYSIS; CONFERENCE PAPER; LITHIATION; PRIORITY JOURNAL; REACTION ANALYSIS; RING OPENING; SYNTHESIS;

EID: 0141988919     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200375101453     Document Type: Conference Paper

References (72)

1. (a) E. J. Corey and X.-M. Cheng. The Logic of Chemical Synthesis, Wiley, New York (1989);
2. (b) K. C. Nicolaou and E. J. Sorensen. Classic in Total Synthesis, VCH, Weinheim (1996).
3. See, for instance, "Aims and Scope". In Adv. Synth. Catal. 343, A3 (2001): "While total synthesis reached extraordinary levels of sophistication in the last century, the development of practical and efficient synthetic methodologies is still in its infancy" (R. Noyori, Ed.).
4. A. Boudier, L. O. Bromm, L. Lotz, P. Knochel. Angew. Chem., Int. Ed. 39, 4414 (2000).
5. For some monographs on organolithium chemistry, see: (a) B. J. Wakefield. Organolithium Methods, Academic Press, London (1988);
6. (b) Lithium Chemistry. A Theoretical and Experimental Overview, A.-M. Sapse and P. von Ragué Schleyer (Eds.), Wiley, Chichester (1995);
7. (c) J. Clayden. Organolithiums: Selectivityfor Synthesis, Pergamon Press, Oxford (2002).
8. For reviews on functionalized organolithium compounds, see: (a) C. Nájera and M. Yus. Trends Org. Chem. 2, 155 (1991);
9. (b) C. Nájera and M. Yus. Recent Res. Devel. Org. Chem. 1, 67 (1997);
10. (c) M. Yus and F. Foubelo. Rev. Heteroatom Chem. 17, 73 (1997);
11. (d) C. Nájera and M. Yus. Curr. Org. Chem. 7, 867 (2003).
12. First account from our laboratory: M. Yus and D. J. Ramón. J. Chem. Soc., Chem. Commun. 398 (1991).
13. For reviews on arene-catalyzed reactions, see: (a) M. Yus. Chem. Soc. Rev. 25, 155 (1996);
14. (b) D. J. Ramón and M. Yus. Eur. J. Org. Chem. 225 (2000).
15. (c) M. Yus. Synlett 1197 (2001);
16. (d) M. Yus and D. J. Ramón. Latv. J. Chem. 79 (2002);
17. (e) D. J. Ramón and M. Yus. Rev. Cubana Quim. 14, 75 (2002);
18. (f) M. Yus. In The Chemistry of Organolithium Compounds, Z. Rappoport and I. Marek (Eds.), Wiley, Chichester (2003). In press.
19. For mechanistic studies, see: (a) M. Yus, R. P. Herrera, A. Guijarro. Tetrahedron Lett. 42, 3455 (2001);
20. (b) M. Yus, R. P. Herrera, A. Guijarro. Chem. Eur. J. 8, 2574 (2002);
21. (c) R. P. Herrera, A. Guijarro, M. Yus. Tetrahedron Lett. 44, 1309 (2003);
22. (d) R. P. Herrera, A. Guijarro, M. Yus. Tetrahedron Lett. 44, 1313 (2003).
23. For a polymer-supported, arene-catalyzed version of this reaction, see: (a) C. Gómez, S. Ruiz, M. Yus. Tetrahedron Lett. 39, 1397 (1998);
24. (b) C. Gómez, S. Ruiz, M. Yus. Tetrahedron 55, 7017 (1999);
25. (c) M. Yus, C. Gómez, P. Candela. Tetrahedron 58, 6207 (2002);
26. (d) T. Arnauld, A. G. M. Barrett, B. T. Hopkins. Tetrahedron Lett. 43, 1081 (2002).
27. For a review, see: D. Guijarro and M. Yus. Recent Res. Devel. Org. Chem. 2, 713 (1998).
28. For a review, see: F. Foubelo and M. Yus. Trends Org. Chem. 7, 1 (1998).
29. A. Guijarro, C. Gómez, M. Yus. Trends Org. Chem. 8, 65 (2000).
30. F. Alonso, P. Candela, C. Gómez, M. Yus. Adv. Synth. Catal. 345, 275 (2003), and references cited therein.
31. F. Alonso, C. Vitale, G. Radivoy, M. Yus. Synthesis 443 (2003).
32. D. Seebach. Angew. Chem., Int. Ed. Engl. 18, 239 (1979).
33. (a) A. Bachki, F. Foubelo, M. Yus. Tetrahedron: Asymmetry 6, 1907 (1995);
34. (b) A. Bachki, F. Foubelo, M. Yus. Tetrahedron: Asymmetry 6, 2997 (1996).
35. See, for instance: K. Sato, K. Suzuki, M. Ueda, M. Katayama, Y. Kajihara. Chem. Lett. 1469 (1991).
36. (a) T. Soler, A. Bachki, L. R. Falvello, F. Foubelo, M. Yus. Tetrahedron: Asymmetry 9, 3939 (1998);
37. (b) T. Soler, A. Bachki, L. R. Falvello, F. Foubelo, M. Yus. Tetrahedron: Asymmetry 11, 493 (2000).
38. (a) L. R. Falvello, F. Foubelo, T. Soler, M. Yus. Tetrahedron: Asymmetry 11, 2063 (2000);
39. (b) M. Yus, T. Soler, F. Foubelo. Tetrahedron: Asymmetry 12, 801 (2001).
40. (a) J. Almena, F. Foubelo, M. Yus. Tetrahedron Lett. 34, 1649 (1993);
41. (b) J. Almena, F. Foubelo, M. Yus. J. Org. Chem. 59, 3210 (1994).
42. P. Beak and A. I. Meyers. Acc. Chem. Res. 19, 356 (1986).
43. R. W. Hoffmann, T. Rühe, F. Chemla, T. Zahneisen. Liebigs Ann. Chem. 719 (1992).
44. For a review, see: F. Alonso and M. Yus. Recent Res. Devel. Org. Chem. 1, 397 (1997).
45. J. Almena. Ph.D. dissertation, Universidad de Alicante (1996).
46. A. Bachki, L. R. Falvello, F. Foubelo, M. Yus. Tetrahedron: Asymmetry 8, 2633 (1997).
47. J. Almena, F. Foubelo, M. Yus. Tetrahedron 50, 5775 (1994).
48. See, for instance: R. B. Bates, L. M. Kroposky, D. E. Potter. J. Org. Chem. 48, 609 (1972).
49. J. Almena, F. Foubelo, M. Yus. Tetrahedron 53, 5563 (1997).
50. D. J. Ramón and M. Yus. Tetrahedron 48, 3585 (1992).
51. J. Almena, F. Foubelo, M. Yus. Tetrahedron 51, 3351 (1995).
52. M. Yus, T. Soler, F. Foubelo. Tetrahedron 58, 7009 (2002).
53. F. Foubelo, C. Gómez, A. Gutierrez, M. Yus. J. Heterocycl. Chem. 37, 1061 (2000).
54. (a) I. M. Pastor and M. Yus. Tetrahedron Lett. 41, 1589 (2000);
55. (b) I. M. Pastor and M. Yus. Tetrahedron 57, 2371 (2001).
56. J. Gomis, I. M. Pastor, M. Yus. Tetrahedron 57, 5799 (2001).
57. M. Yus and J. Gomis. Eur. J. Org. Chem. 1989 (2002).
58. M. Yus and J. Gomis. Eur. J. Org. Chem. 2043 (2003).
59. (a) A. Bachki, F. Foubelo, M. Yus. Tetrahedron Lett. 39, 7759 (1998);
60. (b) M. Yus, F. Foubelo, J. V. Ferrández, A. Bachki. Tetrahedron 58, 4907 (2002).
61. M. Yus, F. Foubelo, J. V. Ferrández. Eur. J. Org. Chem. 2809 (2001).
62. J. Almena, F. Foubelo, M. Yus. Tetrahedron 52, 8545 (1996).
63. J. Almena, F. Foubelo, M. Yus. J. Org. Chem. 61, 1859 (1996).
64. J. Almena, F. Foubelo, M. Yus. Tetrahedron 51, 3365 (1995).
65. M. Yus, F. Foubelo, J. V. Ferrández, A. Bachki. Tetrahedron 58, 4907 (2002).
66. M. Yus and F. Foubelo. Tetrahedron Lett. 42, 2469 (2001).
67. J. F. Gil, D. J. Ramón, M. Yus. Tetrahedron 49, 9535 (1993).
68. J. F. Gil, D. J. Ramón, M. Yus. Tetrahedron 50, 3437 (1994).
69. P. K. Choudhury, J. Almena, F. Foubelo, M. Yus. Tetrahedron 53, 17373 (1997).
70. (a) M. Yus, F. Foubelo, J. V. Ferrández. Chem. Lett. 726 (2002);
71. (b) M. Yus, F. Foubelo, J. V. Ferrández. Tetrahedron 59, 2083 (2003).
72. M. Yus, F. Foubelo, J. V. Ferrández. Tetrahedron Lett. 43, 7205 (2002).