Tandem Cyclization-Cycloaddition Reaction of Rhodium Carbenoids. Scope and Mechanistic Details of the Process

Journal of the American Chemical Society

Volumn 112, Issue 8, 1990, Pages 3100-3109

  Padwa, Albert ^a   Fryxell, Glen E ^a   Zhi, Lin ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METAL COMPLEX; RHODIUM;

ARTICLE; CHEMICAL STRUCTURE; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; QUANTUM MECHANICS;

EID: 0025108625     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00164a034     Document Type: Article

References (79)

1. Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
2. Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol 3, Chapter 6.
3. Semple, J. E.; Joullie, M. M. Heterocycles 1980, 14, 1825.
4. Bartlett, P. A.; Myerson, J. J. Am. Chem. Soc. 1978, 100, 3950.
5. Rychnovsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963.
6. Williams, D. R.; Harigaya, Y.; Moore, J. L.; D'sa, A. J. Am. Chem. Soc. 1984, 106, 2641.
7. Dolle, R. E.; Nicolaou, K. C. J. Am. Chem. Soc. 1986, 108, 2105.
8. Schreiber, S. L.; Sammakia, T.; Hulin, B.; Schulte, G. J. Am. Chem. Soc. 1986, 108, 2106.
9. Noda, I.; Horita, K.; Oikawa, Y.; Yonemitsu, O. Tetrahedron Lett. 1986, 1917.
10. Hopkins, M. H.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 4748.
11. Westley, J. W. Polyether Antibiotics: Naturally Occurring Acid lonophores; Marcel Dekker, New York, 1982; Vol. I-II.
12. Kishi, Y.; Schmid, G.; Fukuyama, T.; Akasaka, K. J. Ant. Chem. Soc. 1979, 101, 259.
13. Lin, Y. Y.; Risk, M.; Ray, S. M.; Engen, D. V.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773.
14. Shimizu, Y.; Chou, H. N.; Bando, H.; Duyne, G. V.; Clardy, J. J. Am. Chem. Soc. 1986, 108, 514.
15. Moore, R. E. Marine Natural Products; Chemical and Biological Perspectives; Scheuer, P. J., Ed.; Academic Press: New York, 1978; Vol. I.
16. Bartlett, P. A. Tetrahedron 1980, 36, 2.
17. Piers, E.; Karunaratne, V. J. J. Org. Chem. 1983, 48, 1774.
18. Magnus, P.; Gange, D.; Bass, L.; Arnold, E. V.; Clardy, J. J. Am. Chem. Soc. 1980, 102, 2134.
19. Gange, D.; Magnus, P. J. Am. Chem. Soc. 1978, 100, 7746.
20. Bruckner, C.; Reissig, H. U.; J. Org. Chem. 1988, 53, 2440.
21. Piers, E.; Karunaratne, V. J. Org. Chem. 1983, 48, 1774.
22. Fugami, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1987, 809.
23. Eberbach, W.; Burchardt, B. Chem. Ber. 1978, 111, 3665.
24. Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1974, 13, 627.
25. Ochiai, H.; Nishihara, T.; Tamaru, Y.; Yoshida, Z. J. Org. Chem. 1988, 523, 1343.
26. Drewes, S. E.; Hoole, R. P. A. Synth. Commun. 1985, 15, 1067.
27. Trost, B. M.; King, S. A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902.
28. 1, 3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley-Interscience: New York, 1984.
29. Padwa, A.; Carter, S. P.; Nimmesgern, H. J. Org. Chem. 1986, 51, 1157.
30. Padwa, A.; Carter, S. P.; Nimmesgern, H.; Stull, P. J. Am. Chem. Soc. 1988, 110, 2894.
31. Ibata, T.; Motoyama, T.; Hamaguchi, M. Bull. Chem. Soc. Jpn. 1976, 49, 2998.
32. Ibata, T.; Toyoda, J. Chem. Lett. 1983, 1453.
33. Ibata, T.; Liu, M. T. H.; Toyoda, J. Tetrahedron Lett. 1986, 4383.
34. Ueda, K.; Ibata, T.; Takebayashi, M. Bull. Chem. Soc. Jpn. 1972, 45, 2779.
35. Ibata, T.; Jitsuhiro, K.; Tsubokura, Y. Bull. Chem. Soc. Jpn. 1981, 54, 240.
36. Padwa, A.; Hornbuckle, S. F.; Fryxell, G. E.; Stull, P. D. J. Org. Chem. 1989, 54, 817.
37. Padwa, A.; Chinn, R. C.; Hornbuckle, S. F.; Zhi, L. Tetrahedron Lett. 1989, 301.
38. Padwa, A.; Hertzog, D. L.; Chinn, R. C. Tetrahedron Lett. 1989, 4077.
39. Padwa, A.; Chinn, R. C.; Zhi, L. Tetrahedron Lett. 1989, 1491.
40. Padwa, A.; Dean, D. C.; Zhi, L. J. Am. Chem. Soc. 1989, 111, 6451.
41. Padwa, A.; Dean, D. C.; Krumpe, K. E. J. Chem. Soc., Chem. Commun. 1989, 921.
42. Padwa, A.; Stull, P. D. Tetrahedron Lett. 1987, 5407.
43. Gilion, A.; Ovadia, D.; Kapon, M.; Bien, S. Tetrahedron 1982, 38, 1477.
44. Maier, M. E.; Evertz, K. Tetrahedron Lett. 1988, 1677.
45. Taylor, K. G. Tetrahedron 1982, 38, 159.
46. Padwa, A.; Fryxell, G. E.; Zhi, L. J. Org. Chem. 1988, 53, 2875.
47. Mander, L. N.; Sethi, P. Tetrahedron Lett. 1983, 5425.
48. Ibata, T.; Toyoda, J.; Sawada, M.; Tanaka, J. J. Chem. Soc., Chem. Commun. 1986, 1266.
49. Maas, G. Topics in Current Chemistry; Springer-Verlag: Berlin, West Germany, 1987.
50. Doyle, M. P. Acc. Chem. Res. 1986, 19, 348.
51. Chem. Rev. 1986, 86, 919.
52. Paulissen, R.; Reimlinger, H.; Hayez, E.; Hubert, A. J.; Teyssié, P. Tetrahedron Lett. 1973, 2233.
53. Hubert, A. J.; Noels, A. F.; Anciaux, A. J.; Teyssié, P. Synthesis 1976, 600.
54. J. Chem. Soc., Chem. Commun. 1980, 765.
55. Anciaux, A. J.; Hubert, A. F.; Noels, N.; Petiniot, N.; Teyssié, P. J. Org. Chem. 1980, 45, 695.
56. Christoph, C. G.; Yoh, Y. B. J. Am. Chem. Soc. 1979, 101, 1422.
57. Johnson, S. A.; Hunt, H. R.; Neumann, H. M. Inorg. Chem. 1963, 2, 690.
58. Regitz, M.; Hocker, J.; Liedhegener, A. In Organic Synthesis; John Wiley, New York, 1973. Collect. Vol. 5, pp 179-183.
59. Burke, S. D.; Grieco, P. A. Org. React. 1979, 26, 361.
60. Taber, D. F.; Petty, E. H. J. Org. Chem. 1982, 47, 4808.
61. Taber, D. F.; Petty, E. H.; Raman, K. J. Am. Chem. Soc. 1985, 107, 196.
62. Landgrebe, J. A.; Iranmanesh, H. J. Org. Chem. 1978, 43, 1244.
63. Lottes, A. C.; Landgrebe, J. A.; Larsen, K. Tetrahedron Lett. 1989, 4089, 4093.
64. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley-Interscience, New York, 1976.
65. Houk, K. N.; Sims, J.; Duke, R. E.; Strozier, R. W.; George, J. K. J. Am. Chem. Soc. 1973, 95, 7287.
66. Sustmann, R. Tetrahedron Lett. 1971, 2717.
67. Sustmann, R.; Trill, H. Angew Chem., Int. Ed. Engl. 1972, 11, 838.
68. Huisgen, R. J. Org. Chem. 1976, 41, 403.
69. Silverstein, R. M.; Brownlee, R. G.; Bellas, T. E.; Wood, D. L.; Brown, L. E. Science 1968, 159, 889.
70. Wood, D. L.; Browne, L. E.; Ewing, B.; Lindahl, K.; Bedard, W. D.; Tilden, P. E.; Mori, K.; Pittman, G. B.; Hughes, P. R. Science 1976, 192, 896.
71. Vite, J. P.; Renwick, J. A. A. Naturwissenschaften 1971, 58, 418.
72. Payne, T. L.; Coster, J. E.; Richerson, J. V.; Edson, L. J.; Hart, E. R. Environ. Entomol. 1978, 7, 578.
73. Oehlschlager, A. C.; Johnston, B. D. J. Org. Chem. 1987, 52, 940.
74. Adrouny, G. A.; Derbes, V. J.; Jung, R. C. Science 1958, 128, 306.
75. Blum, M. S.; Walker, J. R.; Callahan, P. S.; Novak, A. F. Science 1958, 128, 306.
76. Mundy, B. P.; Bjorklund, M. Tetrahedron Lett. 1985, 3899.
77. Corey, D. J.; Shimoji, K. Tetrahedron Lett. 1983, 169.
78. Chaquin, P.; Morizur, J. P.; Kossanji, J. J. Am. Chem. Soc. 1977, 99, 903.
79. Cohen, T.; Bhupathy, M. Tetrahedron Lett. 1983, 4163.