Diels-alder approach to biaryls: Elucidation of competing tandem [2+2] cycloaddition/[1,3] sigmatropic shift pathway

Journal of Organic Chemistry

Volumn 73, Issue 18, 2008, Pages 7305-7309

  Ashburn, Bradley O ^a   Carter, Rich G ^a   Zakharov, Lev N ^a,b  

^a OREGON STATE UNIVERSITY   (United States)

^b UNIVERSITY OF OREGON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE;

[2 + 2] CYCLOADDITION; BIARYLS; CHEMICAL EQUATIONS; CYCLO BUTENE; CYCLOREVERSION; DIELS-ALDER APPROACH; ELECTRON-DEFICIENT; ETHYLENE GAS; LIGHT EXPOSURE; OCTADIENE;

CHEMICAL REACTIONS;

2 HALO 6 NITROPHENYLACETYLENE; ACETYLENE DERIVATIVE; ALKENE DERIVATIVE; BICYCLO COMPOUND; BICYCLO[4.2.0]OCTADIENE; CYCLOBUTENE; CYCLOOCTATRIENE; ETHYLENE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DIELS ALDER REACTION; LIGHT EXPOSURE; PHOTOLYSIS; REACTION ANALYSIS; THERMAL EXPOSURE;

BIPHENYL COMPOUNDS; CYCLIZATION; CYCLOBUTANES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 52449101649     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801245a     Document Type: Article

References (60)

1. Diels, O.; Alder, K. Liebigs Ann. Chem. 1928, 460, 98-122.
2. (a) Houk, K. N.; Lin, Y. T.; Brown, F. K. J. Am. Chem. Soc. 1986, 108, 554-556.
3. (b) Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682-708.
4. (c) Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1993, 115, 7478-7485.
5. (d) Houk, K. N.; Gonzalez, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81-90.
6. (e) Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036-6043.
7. (f) Karadakov, P. B.; Cooper, D. L.; Gerratt, J. J. Am. Chem. Soc. 1998, 120, 3975-3981.
8. (g) Sakai, S. J. Phys. Chem. A 2000, 104, 922-927.
9. (a) Daniel, H.; Jones, G. O.; Houk, K. N. Adv. Synth. Cat. 2006, 348, 2337-2361.
10. (b) Sauer, J. Angew. Chem., Int. Ed. 1967, 6, 16-33.
11. (c) Holmes, H. L. Org. React. 1958, 4, 60-173.
12. Boger, D. L.; Patel, M. Prog. Heterocycl. Chem. 1989, 1, 30-64.
13. Nicholas, P. P.; Carroll, R. T. J. Org. Chem. 1968, 33, 2345-2349.
14. For a recent study into the conformational selectivity in Diels-Alder reactions, see: Bradley, A. Z.; Kociolek, M. G.; Johnson, R. P. J. Org. Chem. 2000, 65, 7134-7138.
15. Allen, C. F. J. Chem. Educ. 1933, 10, 494-497.
16. Moffett, R. B. Org. Synth. 1963, Coll. Vol. IV, 238-241.
17. (a) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401.
18. (b) Trost, B. M.; Jiang, C. Synthesis 2006, 369-396.
19. (a) Ashburn, B. O.; Carter, R. G. Angew. Chem., Int. Ed. 2006, 45, 6737-6741.
20. (b) Ashburn, B. O.; Carter, R. G.; Zakharov, L. N. J. Am. Chem. Soc. 2007, 129, 9109-9116.
21. (c) Naffziger, M. R.; Ashburn, B. O.; Perkins, J. R.; Carter, R. G. J. Org. Chem. 2007, 72, 9857-9865.
22. (d) Ashburn, B. O.; Carter, R. G. J. Org. Chem. 2007, 72, 10220-10223.
23. (e) Perkins, J. R.; Carter, R. G. J. Am. Chem. Soc. 2008, 130, 3290-3291.
24. (f) For a detailed discussion of the importance of the o-nitro moiety, see: Ashburn, B. O.; Carter, R. G. Org. Biomol. Chem. 2008, 6, 255-257.
25. (g) Ashburn, B. O.; Rathbone, L. K.; Camp, E. H.; Carter, R. G. Tetrahedron 2008, 64, 856-865.
26. Prior examples of using a Diels-Alder reaction to construct a biaryl: (a) Reed, J. A.; Schilling, C. L.; Tarvin, R. F.; Rettig, T. A.; Stille, J. K. J. Org. Chem. 1969, 34, 2188-2192.
27. (b) McDonald, E.; Suksamrarn, A.; Wylie, R. D. J. Chem. Soc., Perkin Trans. 1 1979, 1893-1900.
28. (c) Weinreb, S. M.; Basha, F. Z.; Hibino, S.; Khatri, N. A.; Kim, D.; Pye, W. E.; Wu, T. T. J. Am. Chem. Soc. 1982, 104, 536-544.
29. (d) Boger, D. L.; Panek, J. S.; Duff, S. R. J. Am. Chem. Soc. 1985, 107, 5745-5754.
30. (e) Effenberger, F.; Ziegler, T. Chem. Ber. 1987, 120, 1339-1346.
31. (f) Kanakam, C. C.; Mani, N. S.; Ramanathan, H.; Subba Rao, G. S. R. J. Chem. Soc., Perkin Trans. I 1989, 1907-1913.
32. (g) Sain, B.; Sandhu, J. S. J. Org. Chem. 1990, 55, 2545-2546.
33. (h) Bateson, J. H.; Smith, C. F.; Wilkinson, J. B. J. Chem. Soc., Perkin Trans 1 1991, 651-653.
34. (i) Smith, D. M.; Royles, B. J. L. J. Chem. Soc., Perkin Trans. 1 1994, 355-358.
35. (j) D'Auria, M. Tetrahedron Lett. 1995, 36, 6567-6570.
36. (k) Knolker, H.-J.; Baum, E.; Hopfmann, T. Tetrahedron Lett. 1995, 36, 5339-5342.
37. (l) Avenoza, A.; Busto, J. H.; Cativiela, C.; Peregrina, J. M. Synthesis 1995, 671-674.
38. (m) Balázs, L.; Kádas, I.; Tõke, L. Tetrahedron Lett. 2000, 41, 7583-87.
39. (n) Watson, M. D.; Fechtenkotter, A.; Mullen, K. Chem. Rev. 2001, 101, 1267-1300.
40. (o) Min, S.-H.; Kim, Y.-W.; Choi, S.; Park, K. B.; Cho, C.-G. Bull. Korean Chem. Soc. 2002, 23, 1021-1022.
41. (p) Hilt, G.; Smolko, K. I. Synthesis 2002, 686-92.
42. (q) Hilt, G.; Smolko, K. I.; Lotsch, B. V. Synlett 2002, 1081-1084.
43. (r) Moore, J. E.; York, M.; Harrity, J. P. A. Synlett 2005, 860-62.
44. (s) Yamato, T.; Miyamoto, M.; Hironaka, T.; Miura, Y. Org. Lett. 2005, 7, 3-6.
45. (t) Hilt, G.; Galbiati, F.; Harms, K. Synthesis 2006, 3575-3584.
46. (u) Liu, Y.; Lu, K.; Dai, M.; Wang, K.; Wu, W.; Chen, J.; Quan, J.; Yang, Z. Org. Lett. 2007, 9, 805-808.
47. Pearson, A. J.; Sun, H. J. Org. Chem. 2007, 72, 7693-7700.
48. (a) Ficini, J.; Dureault, A.; Revial, G.; Touzin, A. M. Tetrahedron Lett. 1974, 1025-1027.
49. (b) Kivala, M.; Boudon, C.; Gisselbrecht, J.-P.; Seiler, P.; Gross, M.; Diederich, F. Chem. Commun. 2007, 4731-4733.
50. See the Supporting Information for ORTEP representation of cyclobutene 15.
51. Banwell, M. G.; Lupton, D. W.; Ma, X.; Renner, J.; Sydnes, M. O. Org. Lett. 2004, 6, 2741-2744.
52. Aldrich Cat. No. 299634-1G: Furuta, T.; Kitamura, Y.; Hashimoto, A.; Fujii, S.; Tanaka, K.; Kan, T. Org. Lett. 2007, 9, 183-186.
53. See the Supporting Information for ORTEP representation of cyclobutene 25.
54. Baldwin, J. E.; Leber, P. A. Org. Biomol. Chem. 2008, 6, 36-47.
55. The molecular modelling program Spartan '06 was used to carry out the Density Functional B3LYP calculations. The 6-31G** basis set was chosen to perform the geometry optimization. Computations were performed with a Linux workstation running Spartan version '06.
56. Wender, P. A.; Leichleiter, J. C. J. Am. Chem. Soc. 1977, 99, 267-68.
57. This result was also observed in the initial reaction of acetylene 13 and diene 11 (Scheme 1).
58. Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 395-397.
59. (a) Tidwell, T. T. Eur. J. Org. Chem. 2006, 56, 3-576.
60. (b) Holder, R. W. J. Chem. Educ. 1976, 53, 81-85.