An ab Initio Study of Facial Selectivity in the Diels-Alder Reaction

Journal of Organic Chemistry

Volumn 63, Issue 1, 1998, Pages 105-112

  Xidos, James D ^a   Poirier, Raymond A ^a   Pye, Cory C ^a   Jean Burnell, D ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001489122     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9712815     Document Type: Article

References (77)

1. (a) Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction; John Wiley & Sons, New York, 1990.
2. (b) Fallis, A. G.; Lu, Y.-F. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press, Greenwich, CT, 1993; Vol. 3, pp 1-66.
3. (a) Gleiter, R.; Paquette, L. A. Acc. Chem. Res. 1983, 16, 328-334.
4. (b) Paquette, L. A.; Gugelchuk, M. J. Org. Chem. 1988, 53, 1835-1837.
5. (c) Hickey, E. R.; Paquette, L. A. Tetrahedron Lett. 1994, 35, 2309-2312.
6. (d) Paquette, L. A.; Hickey, E. R. Tetrahedron Lett. 1994, 35, 2313-2316.
7. (a) Sugimoto, T.; Kobuke, Y.; Furukawa, J. J. Org. Chem. 1976, 41, 1457-1459.
8. (b) Watson, W. H.; Galloy, J.; Bartlett, P. D.; Roof, A. A. M. J. Am. Chem. Soc. 1981, 103, 2022-2031.
9. (c) Hagenbuch, J.-P.; Vogel, P.; Pinkerton, A. A.; Schwarzenbach, D. Helv. Chim. Acta 1981, 64, 1818-1832.
10. Brown, F. K.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 1971-1978.
11. Ginsburg, D. Tetrahedron 1983, 39, 2095-2135.
12. Cossu, S.; Cuomo, G.; De Lucchi, O.; Maggini, M.; Valle, G. J. Org. Chem. 1996, 61, 153-158.
13. Coxon, J. M.; Fong, S. T.; McDonald, D. Q.; Steel, P. J. Tetrahedron Lett. 1993, 34, 163-166.
14. (a) Winstein, S.; Shatavsky, M.; Norton, C.; Woodward, R. B. J. Am. Chem. Soc. 1955, 77, 4183-4184.
15. (b) Mironov, V. A.; Dolgaya, M. E.; Lukyanov, V. T.; Yankovskii, S. A. Zh. Organich. Khim. 1976, 12, 1436-1442.
16. (c) Jones, D. W. J. Chem. Soc., Chem. Commun. 1980, 739-740.
17. (d) Harvey, D. F.; Grezner, E. M. J. Org. Chem. 1996, 61, 159-165.
18. McClinton, M. A.; Sik, V. J. Chem. Soc., Perkin Trans. 1 1992, 1891-1895.
19. (a) Williamson, K. L.; Hsu, Y.-F. L.; Lacko, R.; Youn, C. H. J. Am. Chem. Soc. 1969, 91, 6129-6138.
20. (b) Williamson, K. L.; Hsu, Y.-F. L. J. Am. Chem. Soc. 1970, 92, 7385-7389.
21. (c) Facial selectivity for 5-methyl-1,3-cyclopentadiene was rationalized by analogy with the chloro-diene in: Ford, W. T. J. Org. Chem. 1971, 36, 3979-3987.
22. (a) Breslow, R.; Hoffman, J. M., Jr. J. Am. Chem. Soc. 1972, 94, 2110-2111.
23. (b) Breslow, R.; Hoffman, J. M., Jr.; Perchonock, C. Tetrahedron Lett. 1973, 3723-3726.
24. (c) Franck-Neumann, M.; Sedrati, M. Tetrahedron Lett. 1983, 24, 1391-1394.
25. Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 1136-1144.
26. Wellman, M. A.; Burry, L. C.; Letourneau, J. E.; Bridson, J. N.; Miller, D. O.; Burnell, D. J. J. Org. Chem. 1997, 62, 939-946.
27. Ishida, M.; Tomohiro, S.; Shimizu, M.; Inagaki, S. Chem. Lett. 1995, 739-740.
28. (a) Ishida, M.; Aoyama, T.; Kato, S. Chem. Lett. 1989, 663-666.
29. (b) Ishida, M.; Beniya, Y.; Inagaki, S.; Kato, S. J. Am. Chem. Soc. 1990, 112, 8980-8982.
30. (c) Ishida, M.; Aoyama, T.; Beniya, Y.; Yamabe, S.; Kato, S.; Inagaki, S. Bull. Chem. Soc. Jpn. 1993, 66, 3430-3439.
31. (d) Ishida, M.; Kakita, S.; Inagaki, S. Chem. Lett. 1995, 469-470.
32. (e) For addition of a chiral nitroso dienophile to the SMe-substituted cyclopentadiene, see: King, S. B.; Ganem, B. J. Am. Chem. Soc. 1991, 113, 5089-5090.
33. (a) Ashe III, A. J. J. Am. Chem. Soc. 1970, 92, 1233-1235.
34. (b) Fleming, I.; Michael, J. P. J. Chem. Soc., Chem. Commun. 1978, 245-247.
35. (c) Magnus, P.; Cairns, P. M.; Moursounidis, J. J. Am. Chem. Soc. 1987, 109, 2469-2471.
36. Burry, L. C.; Bridson, J. N.; Burnell, D. J. J. Org. Chem. 1995, 60, 5931-5934.
37. Gulard, J. R.; Burnell, D. J. Can. J. Chem. 1992, 70, 1296-1307.
38. (a) Gillard, J. R.; Newlands, M. J.; Bridson, J. N.; Burnell, D. J. Can. J. Chem. 1991, 69, 1337-1343.
39. (b) Pye, C. C.; Xidos, J. D.; Poirier, R. A.; Burnell, D. J. J. Phys. Chem. A 1997, 101, 3371-3376.
40. (a) Burnell, D. J.; Valenta, Z. J. Chem. Soc., Chem. Commun. 1985, 1247-1248.
41. (b) Burnell, D. J.; Goodbrand, H. B.; Kaiser, S. M.; Valenta, Z. Can. J. Chem. 1987, 65, 154-165.
42. (c) Burnell, D. J.; Valenta, Z. Can. J. Chem. 1991, 69, 179-184.
43. (d) Letourneau, J. E.; Wellman, M. A.; Burnell, D. J. J. Org. Chem. 1997, 62, 7272-7277.
44. Brown, F. K.; Houk, K. N.; Burnell, D. J.; Valenta, Z. J. Org. Chem. 1987, 52, 3050-3059.
45. (a) McLean S.; Haynes, P. Tetrahedron 1965, 21, 2313-2327.
46. (b) Krow, G. R.; Carey, J. T.; Zacharias, D. E.; Knaus, E. E. J. Org. Chem. 1982, 47, 1989-1993.
47. (c) Yates, P.; Gomes, A.; Burnell, D. J.; Gong, D. D.; Sawyer, J. F. Can. J. Chem. 1989, 67, 37-47.
48. (d) Paquette, L. A.; Vanucci, C.; Rogers, R. D. J. Am. Chem. Soc. 1989, 111, 5792-5800.
49. (e) Adam, W.; Jacob, U.; Prein, M. J. Chem. Soc., Chem. Commun. 1995, 839-840.
50. Inagaki, S.; Fujimoto, H.; Fukui, K. J. Am. Chem. Soc. 1976, 98, 4054-4061.
51. Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663-666.
52. (a) Koizumi, T.; Arai, Y.; Takayama, H.; Kuriyama, K.; Shiro, M. Tetrahedron Lett. 1987, 28, 3689.
53. (b) Naperstkow, A. M.; Macaulay, J. B.; Newlands, M. J.; Fallis, A. G. Tetrahedron Lett. 1989, 30, 5077-5080.
54. Werstiuk, N. H.; Ma, J.; Macaulay, J. B.; Fallis, A. G. Can. J. Chem. 1992, 70, 2798-2808.
55. Anh, N. T. Tetrahedron 1973, 29, 3227-3232.
56. Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552.
57. (a) Chung, W.-S.; Turro, N. J.; Srivastava, S.; Li, H.; le Noble, W. J. J. Am. Chem. Soc. 1988, 110, 7882-7883.
58. (b) Halterman, R. L.; McCarthy, B. A.; McEvoy, M. A. J. Org. Chem. 1992, 57, 5585-5589.
59. Werstiuk, N. H.; Ma, J. Can. J. Chem. 1994, 72, 2493-2505.
60. Poirier, R. A.; Pye, C. C.; Xidos, J. D.; Burnell, D. J. J. Org. Chem. 1995, 60, 2328-2329.
61. (a) Poirier, R. A.; Peterson, M. R. MUNGAUSS, 1990 and Poirier, R. A.; Wang, Y.; Pye, C. C. MUNGAUSS V1.0; Department of Chemistry, Memorial University of Newfoundland: St. John's, Newfoundland, Canada,
62. (b) Colonna, F.; Jolly, L.-H.; Poirier, R. A.; Angyan, J. G.; Jansen, G. Comput. Phys. Commun. 1994, 81, 293-317.
63. Gaussian 92, Revision A: Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schelgel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J.; Pople, J. A.; Gaussian, Inc., Pittsburgh, PA, 1992.
64. (a) Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; Defrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654-3665, and references therein2E
65. (b) For fourth and fifth period elements, a split valence basis set containing one set of d-polarizing functions (43321/4321/41*) and (433321/43321/431*), respectively, were used: Huzinaga, S.; Andzelm, J.; Klobukowski, M.; Radzio-Andzelm, E.; Sakai, Y.; Tatewaki, H. In Gaussian Basis Sets for Molecular Calculations; Huzinaga, S., Ed.; Elsevier Science: Amsterdam, 1984.
66. Davidon, W. C. Math. Prog. 1975, 9, 1-30.
67. Powell, M. J. D. Subroutine VA05AD, A.E.R.E. Subroutine Library, Harwell; Didcott, Berkshire, U.K.
68. Csaszar, P.; Pulay, P. J. Mol. Struct. 1984, 114, 31-34.
69. Boys, S. F. Quantum Theory of Atoms, Molecules and the Solid State; Löwdin, P. O., Ed.; Academic Press: New York, 1966.
70. X refers to the substituent at C5 of 1,3-cyclopentadiene. The C-X bond refers to the bond from C5 of 1,3-cyclopentadiene to the central atom of the substituent.
71. Individual activation energies computed at the Hartree-Fock level must contain systematic errors, but syn-anti ratios are ideally suited for comparison because of the isodesmic relationship of facial diastereoselectivity.
72. Boyd, R. J.; Edgecombe, K. E. J. Am. Chem. Soc. 1988, 110, 4182-4186. For hydrogen and fifth Period atoms: Allred, A. L.; Rochow, E. G. J. Inorg. Nucl. Chem. 1958, 5, 264-268.
73. Boyd, R. J.; Edgecombe, K. E. J. Am. Chem. Soc. 1988, 110, 4182-4186. For hydrogen and fifth Period atoms: Allred, A. L.; Rochow, E. G. J. Inorg. Nucl. Chem. 1958, 5, 264-268.
74. 3 and in a MP4SDQ/431G study of the Diels-Alder reaction of 1,3-butadiene with acetylene: Coxon, J. M.; Grice, S. T.; Maclagan, R. G. A. R.; McDonald, D. Q. J. Org. Chem. 1990, 55, 3804-3807.
75. (a) Förster, H.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1977, 16, 429-441.
76. (b) Gallo, R. Prog. Phys. Org. Chem. 1983, 14, 115-163.
77. Robb, M. A.; Haines, W. J.; Csizmadia, I. G. J. Am. Chem. Soc. 1973, 95, 42-48.