Tandem Free-Radical Alkene Addition Reactions of Acyl Radicals

Journal of the American Chemical Society

Volumn 112, Issue 10, 1990, Pages 4003-4008

  Boger, Dale L ^a   Mathvink, Robert J ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542645578     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00166a043     Document Type: Article

References (81)

1. Curran, D. P. Synthesis 1988, 417, 489.
2. Giese, B. Radicals in Organic Synthesis; Pergamon Press: New York, 1986.
3. Ramalah, M. Tetrahedron 1987, 43, 3541.
4. Surzur, J.-M. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1982; Vol. 2, Chapter 3.
5. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377.
6. Boger, D.L.; Mathvink, R. J. J. Org. Chem. 1989, 54, 1777.
7. Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328.
8. Fischer, H.; Paul, H. Acc. Chem. Res. 1987, 20, 200.
9. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895.
10. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1988, 29, 2585.
11. Crich, D.; Fortt, S. M.; Ritchie, T. J. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer: Boston, 1989; p 135.
12. Crich, D.; Eustace, K. A.; Ritchie, T. J. Heterocycles 1989, 28, 67.
13. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun. 1989, 1366.
14. Tailhan, C.; Zard, S. Z. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer: Boston, 1989; p 263.
15. Delduc, P.; Tailhan, C.; Zard, S. Z. J. Chem. Soc., Chem. Commun. 1988, 308.
16. Mestre, F.; Tailhan, C; Zard, S. Z. Heterocycles 1989, 28, 171.
17. Bachi, M. D.; Bosch, E.; Denenmark, D.; Girsh, D. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer: Boston, 1989; p 125.
18. Coveney, D. J.; Patel, V. F.; Pattenden, G, Tetrahedron Lett. 1987, 28, 5949.
19. Patel, V. F.; Pattenden, G. Tetrahedron Lett. 1988, 29, 707.
20. Cekovic, Z. Tetrahedron Lett. 1972, 749.
21. Walsh, E. J., Jr.; Messinger, J. M., II; Grudoski, D. A.; Allchin, C. A. Tetrahedron Lett. 1980, 21, 4409.
22. Dulou, R.; Chretien-Bessiere, Y.; Desalbres, H. C. R. Acad. Sci., Ser. C 1964, 258, 603.
23. Montheard, J.-P. C. R. Acad. Sci., Ser. C 1965, 260, 577.
24. Chatzopoulos, M.; Montheard, J.-P. C. R. Acad. Sci., Ser. C 1975, 280, 29.
25. Kampmeier, J. A.; Harris, S. H.; Wedegaertner, D. K. J. Org. Chem. 1980, 45, 315.
26. Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641.
27. Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1988, 29, 2581.
28. Bachi, M. D.; Bosch, E. J. Org. Chem. 1989, 54, 1234.
29. Singh, A. K.; Bakshi, R. K.; Corey, E. J. J. Am. Chem. Soc. 1987, 109, 6187.
30. Nozaki, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 6127.
31. Breslow, R.; Olin, S. S.; Groves, J. T. Tetrahedron Lett. 1968, 1837.
32. Julia, M. Acc. Chem. Res. 1971, 4, 386.
33. Stork, G.; Mook, R., Jr. J. Am. Chem. Soc. 1983, 105, 3720.
34. Beckwith, A. L. J.; Roberts, D. H.; Schiesser, C. H.; Wallner, A. Tetrahedron Lett. 1985, 26, 3349.
35. Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985,107, 1448.
36. Curran, D. P.; Rakiewicz, D. M. Tetrahedron 1985, 41, 3943.
37. Curran, D. P.; Chen, M.-H. Tetrahedron Lett. 1985, 26, 4991.
38. Curran, D. P.; Kuo, S.-C. J. Am. Chem. Soc. 1986,108, 1106.
39. Curran, D. P.; Kuo, S.-C. Tetrahedron 1987, 43, 5653.
40. Winkler, J. D.; Sridar, V. J. Am. Chem. Soc. 1986,108, 1708.
41. Winkler, J. D.; Sridar, V. Tetrahedron Lett. 1988, 29, 6219.
42. Beckwith, A. L. J.; Easton, C. J.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 482.
43. Beckwith, A. L. J.; Blair, I. A.; Phillipou, G. Tetrahedron Lett. 1974, 2251.
44. Baggaley, K. H.; Brooks, S. G.; Green, J.; Redman, B. T. J. Chem. Soc. C 1971, 2671.
45. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765.
46. Stork, G.; Sher, P. M.; Chen, H.-L. J. Am. Chem. Soc. 1986,108,6384.
47. Moriya, O.; Kakihana, M.; Urata, Y.; Sugizaki, T.; Kageyama, T.; Lleno, Y.; Endo, T. J. Chem. Soc., Chem. Commun. 1985,1401.
48. Keck, G. E.; Burnett, D. A. J. Org. Chem. 1987,52, 2958.
49. Togo, H.; Kikuchi, O. Tetrahedron Lett. 1988,29,4133.
50. Togo, H.; Kikuchi, O. Heterocycles 1989, 28, 373.
51. Lopez, J. C.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 3450.
52. Sheldon, R. A.; Kochi, J. K. Organic Reactions; Wiley: New York, 1972; Vol. 19, p 279.
53. San Miguel, B. A.; Maillard, B.; Delmond, B. Tetrahedron Lett. 1987, 28, 2127.
54. Cekovic, Z.; Saicic, R. Tetrahedron Lett. 1986, 27, 5893.
55. Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1985, 980.
56. Curran, D. P.; Van Elburg, P. A. Tetrahedron Lett. 1989, 30, 2501.
57. Curran, D. P.; Chen, M.-H. J. Am. Chem. Soc. 1987,109, 6558.
58. Van Der Linde, L. M.; Van Der Weerdt, A. J. A. Tetrahedron Lett. 1984, 25, 1201.
59. Scheffer, J. R.; Wostradowski, R. A. J. Org. Chem. 1972, 37, 4317
60. Beckwith, A. L. J. Tetrahedron 1981, 37, 3073.
61. Beckwith, A. L. J.; Lawrence, T.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 484.
62. Beckwith, A. L. J.; Phillipou, G.; Serelis, A. K. Tetrahedron Lett. 1981, 22,2811.
63. Rajanbabu, T. V.; Fukunaga, T. J. Am. Chem. Soc. 1989, 111, 296.
64. Rajanbabu, T. V. J. Am. Chem. Soc. 1987, 109, 609. Theoretical treatments:
65. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
66. Spellmeyer, D.C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.
67. Gottschalk, P.; Neckers, D. C. J. Org. Chem. 1985, 50, 3498.
68. Hanessian, S.; Dhanoa, D. S.; Beaulieu, P. L. Can. J. Chem. 1987, 65, 1859.
69. Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 5.
70. Johnson, W. S. Acc. Chem. Res. 1968, 1,1.
71. Johnson, W. S. Angew. Chem., Int. Ed. Engl. 1976,15,9.
72. Van Tamelen, E. E. Acc. Chem. Res. 1968,1, 111.
73. Lansbury, P. T. Acc. Chem. Res. 1972, 5, 311.
74. Chamberlin, A. R.; Bloom, S. H.; Cervini, L. A.; Fotsch, C. H. J. Am. Chem. Soc. 1988, 110, 4788 and references cited therein
75. Saito, S.; Hirohara, Y.; Narahara, O.; Moriwake, T. J. Am. Chem. Soc. 1989, 111, 4533.
76. Posner, G. H.; Shulman-Roskes, E. M. J. Org. Chem. 1989, 54, 3514.
77. Zhang, Y.; Negishi, E. J. Am. Chem. Soc. 1989, 111, 3454.
78. Trost, B. M.; Lee, D. C. J. Am. Chem. Soc. 1988, 110, 7255.
79. Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328.
80. Still, W.C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
81. Reichel, C. J.; Bryson, T. A. Heterocycles 1982, 18, 277.