Acyclic Stereochemical Control in Free-Radical Reactions

Accounts of Chemical Research

Volumn 24, Issue 10, 1991, Pages 296-304

  Porter, Ned A ^a,b,c   Giese, Bernd ^a,b,c   Curran, Dennis P ^a,b,c  

^a DUKE UNIVERSITY   (United States)

^b UNIVERSITY OF BASEL   (Switzerland)

^c UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 12044254102     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar00010a003     Document Type: Article

References (95)

1. Gomberg, M. J. Am. Chem. Soc. 1900, 22, 757.
2. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press: New York, 1986.
3. Curran, D. P. Synthesis 1988, 417–439, 489–513.
4. Curran, D. P. In Comprehensive Organic Chemistry: Selectivity, Strategy and Efficiency in Modern Organic Chemistry; Trost, B., Fleming, I., Eds.; Pergamon: New York; Vol. 4, Chapters 4.1 and 4.2, in press.
5. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev., in press.
6. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901.
7. Crich, D. Aldrichimica Acta 1987, 20, 35.
8. Keck, G. E.; Yates, J. B. J. Am. Chem. Soc. 1982, 104, 5829.
9. Grignon, J.; Servens, C.; Pereyre, M. J. Organomet. Chem. 1975, 96, 225.
10. Baldwin, J. E.; Kelly, D. R. J. Chem. Soc, Chem. Commun. 1985, 682.
11. Snider, B. B.; Mohan, R.; Kates, S. A. J. Org. Chem. 1985, 50, 3559.
12. Heiba, E. I.; Dessau, R. M.; Rodewald, P. G. J. Am. Chem. Soc 1974, 96, 7977.
13. Beckwith, A. L. J.; Ingold, K. U. Rearrangements in Ground and Excited States; deMayo, P., Ed.; Academic Press: New York, 1980; Vol. 1, p 162.
14. Hart, D. J. Science 1984, 223, 883.
15. Stork, G. Selectivity-A Goal For Synthetic Efficiency; Bartman, W. T. B., Trost, B., Eds.; VCH: Weinheim, 1984.
16. Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969.
17. Julia, M.; Maumy, M. Bull. Soc. Chim. Fr. 1969, 2415.
18. Hart, D. J.; Huang, H. C. Tetrahedron Lett. 1985, 26, 3749.
19. Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205.
20. Vassen, R.; Runsink, J.; Scharf, H.-D. Chem. Ber. 1986, 119, 3492.
21. Kruk, C.; Spaargaren, K. Spectrochim. Acta 1971, 27A, 77.
22. Strub, W.; Roduner, R.; Fischer, H. J. Phys. Chem. 1987, 91, 4379 and references cited therein.
23. Ruchardt, C.; Beckhaus, H.-D. Top. Curr. Chem. 1985, 88, 1.
24. Bordweu, F. G.; Harrelson, J. A., Jr. Con. J. Chem. 1990, 68, 1714.
25. Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
26. Evans, D. A. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1984; Vol. 3, p 2.
27. Lumtowski, K. A.; Meyers, A. I. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1984, Vol. 3, p 213.
28. Mukaiyama, T. Challenges in Synthesis Organic Chemistry; Int. Ser. Monographs on Chemistry 20; Oxford University Press: Oxford, 1990.
29. Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624.
30. Oppolzer, W. Tetrahedron 1987, 43, 1969.
31. Curran, D. P.; Heffner, T. A. J. Org. Chem. 1990, 55, 4585.
32. Porter, N. A.; Lacher, B.; Chang, V. H.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309.
33. Porter, N. A.; Scott, D. M.; Lacher, B.; Gieae, B.; Zeifz, H. G.; Lindner, H. J. J. Am, Chem. Soc. 1989, 111, 8311.
34. Porter, N. A.; Scott, D. M.; Rosenstein, I. J.; Giese, B.; Veil, A.; Zeitz, H. G. J. Am. Chem. Soc. 1991, 113, 1791.
35. Scott, D. M.; McPhail, A. T.; Porter, N. A. Tetrahedron Lett. 1990, 31, 1679.
36. Porter, N. A.; Wu, W.-X.; McPhail, A.T. Tetrahedron Lett. 1991, 32, 707.
37. Dewar, M. J. S.; Olivella, S. J. Am. Chem. Soc. 1978, 100, 5290.
38. Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.
39. Pueno, T.; Kamachi, M. Macromolecules 1988, 21, 908.
40. Kawammi, Y.; Kataum, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn, 1987, 60, 4190.
41. Lamy-Schelkens, H.; Ghosez, L. Tetrahedron Lett. 1989, 30, 5891.
42. Veit, A.; Giese, B., unpublished results.
43. Curran, D. P.; Stack, J., unpublished observations.
44. Porter, N. A.; Cullen, B., unpublished observations.
45. Porter, N. A.; Bruhnke, J.; Rosenstein, I. J.; Wu, W.-X.; Breyer, R. J. Am. Chem. Soc, in press.
46. Imwinkelried, R.; Hegedug, L. S. Organometailks 1988, 7, 702.
47. Askew, B.; Ballester, P.; Buhr, C.; Jeong, K. S.; Jones, S.; Paris, K.; Williams, K.; Rebek, J., Jr. J. Am. Chem. Soc. 1989, 111, 1082.
48. Curran, D. P.; Jeong, K.-S.; Heffner, T. A.; Rebek, J., Jr. J. Am. Chem. Soc. 1989, 111, 9238.
49. Stack, J. G.; Curran, D. P., manuscript in preparation.
50. Stack, J. G.; Curran, D. P.; Rebek, J., Jr.; Ballester, P. J. Am. Chem. Soc, in press.
51. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc 1988, 110, 1238.
52. Renaud, P.; Schubert, S. Synlett 1990, 625.
53. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem, Soc. 1990, 112, 6738.
54. Porter, N. A.; Swann, E.; Nally, J.; McPhail, A. T. J. Am. Chem. Soc. 1990, 112, 6740.
55. Porter, N. A.; Breyer, R.; Swann, E.; Allen, T.; Nally, J.; McPhail, A. T. J, Am, Chem. Soc., in press.
56. Giese, B.; Zehnder, M.; Roth, M.; Zeitz, H.-G. J. Am. Chem. Soc. 1990, 112, 6741.
57. Oppolzer, W. Pure Appl. Chem. 1988, 60, 39.
58. Heffner, T. M.S. Thesis, University of Pittsburgh, 1989.
59. Curran, D. P.; Kim, B. H.; Daugherty, J.; Heffner, T. A. Tetrahedron Lett. 1988, 29, 3555.
60. Curran, D. P.; Heffner, T. A. J. Org, Chem, 1990, 55, 4585.
61. Shen, W. Ph.D. Thesis, University of Pittsburgh, 1991.
62. Zhang, J. Ph.D. Thesis, University of Pittsburgh, 1990.
63. Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603.
64. Barton, D. H. R.; Bridon, D.; Fernandez-Picot, I.; Zard, S. Z. Tetrahedron 1987, 43, 2733.
65. Stack, J.; Curran, D. P., manuscript in preparation.
66. Hamon, D. P. G.; Razzino, P.; Massey-Westropp, R. A. J. Chem. Soc, Chem. Commun. 1991, 332.
67. Whitesell, J. K. Acc. Chem. Res. 1985, 18, 280.
68. Beckwith, A. L. J.; Brumby, S. J. Chem. Soc, Perkin Trans. 2 1987, 1801.
69. Bordwell, F. G.; Gallagher, T.; Zhang, T. J. Am. Chem, Soc. 1991, 113, 3495.
70. Podesta, J. C.; Chopa, A. B.; Ayala, A. D. J. Organomet. Chem. 1981, 212, 163.
71. Podesta, J. C.; Chopa, A. B. J. Organomet. Chem. 1982, 229, 223.
72. Chopa, A. B.; Koll, L. C.; Savini, M. C.; Podesta, J. C.; Neumann, W. P. Organometallics 1985, 4, 1036.
73. Gouzoules, F. H.; Whitney, R. A. J. Org. Chem. 1986, 51, 2024.
74. Giese, B.; Meixner, J. Tetrahedron Lett. 1977, 18, 2783.
75. Meixner, J. Ph.D. Thesis, TH Darmstadt, 1980.
76. Bulliard, M.; Zeitz, H.-G.; Giese, B. Synlett 1991, 423.
77. Hart, D. J.; Huang, H. C.; Krishnamurthy, R.; Schwartz, T. J. Am. Chem. Soc. 1989, 111, 7507.
78. Guindon, Y.; Yoakim, C.; Lemieux, R.; Boisvert, L.; Delorme, D.; Lavallee, J.-F. Tetrahedron Lett. 1990, 31, 2845.
79. Guindon, Y. U.; Lavallee, J.-F.; Boisvert, L.; Chabot, L.; Delorme, D.; Yoakim, C.; Hall, D.; Lemieux, R.; Simoneau, B. Tetrahedron Lett. 1991, 32, 27.
80. Seong, C. M. Ph.D. Thesis, University of Pittsburgh, 1990.
81. Curran, D. P.; Seong, C. M. J. Am. Chem. Soc. 1990, 112, 9401.
82. Curran, D. P.; Thoma, G. Tetrahedron Lett., in press.
83. Giese, B.; Bulliard, M.; Zeitz, H.-G. Synlett 1991, 425.
84. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
85. Hart, D. J.; Krishnamurthy, R. Synlett 1991, 412.
86. He, J. Ph.D, Thesis, TH Daimatadt, 1990.
87. Bulliard, M.; Giese, B., unpublished results.
88. Caramella, P.; Rondan, N. G.; Paddon-Row, M. N.; Houk, K. N. J, Am. Chem. Soc. 1981, 103, 2438.
89. Curran, D. P.; Abraham, A.; Liu, H. J. Org. Chem. 1991, 56, 4335.
90. Ramamoorthy, P., unpublished results.
91. Cram, D. J.; Abd Elhafez, F. A. J. Am. Chem. Soc. 1952, 74, 5828.
92. Kulicke, K. J.; Giese, B. Synlett 1990, 91.
93. Giese, B.; Damm, W.; Dickhaut, J.; Wetterich, F.; Sun, S.; Curran, D. P. Tetrahedron Lett, in press.
94. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
95. Anh, N. T.; Eisenstein, O. Mouu. J. Chim. 1977, 1, 61.