Stereospecific synthesis of (+)- and (-)-cyclooctenone derivatives using a ring expansion reaction with Me3SiSnBu3 and CsF

Journal of the American Chemical Society

Volumn 121, Issue 6, 1999, Pages 1217-1225

  Imai, Alice Emi ^a   Sato, Yoshihiro ^a   Nishida, Mayumi ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE; KETONE;

ARTICLE; CHEMICAL REACTION; ISOMERISM; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033577009     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983168h     Document Type: Article

References (77)

1. (a) Petasis, N.; Patane, M. A. Tetrahedron 1992, 48, 5757 and references therein,
2. (b) Ayanogulo, E.; Gebreyesus, T.; Beechan, C.; Djerassi, C, Tetrahedron 1979.35, 1035.
3. (c) Schitz, F.; Hollenbeak, K. H.; Vanderah, D. J. Tetrahedron 1978, 34, 2719.
4. (d) Fenical, W.; Shulte, G. R.; Finer, J.; Clardy, J. J. Org. Chem. 1978, 43, 3628.
5. (a) Kinney, W. A.; Coghlan, M. J.; Paquette, L. A. J. Am. Chem. Soc. 1984, 106, 6868.
6. (b) Kinney, W. A.; Coghlan, M. J.; Paquette, L. A. J. Am. Chem. Soc. 1985, 107, 7352.
7. Paquette, L. A.; Liang, S.; Galatsis, P. Synth. Lett. 1990, 663.
8. (a) Tamborski, C.; Soloski, E. J. J. Org. Chem. 1963, 28, 237.
9. (b) Schumann, H.; Ronecker, S. Z. Naturforsch. B 1967, B22, 452.
10. (c) Chenard, B. L.; Van Zyl, C. M. J. Org. Chem. 1986, 51, 3561.
11. (a) Azizian, H.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1981, 215, 49.
12. (b) Kosugi, M.; Ohya, T.; Migita, T. Bull. Chem. Soc. Jpn. 1983, 56, 3539.
13. (c) Mitchell, T. N.; Killing, H.; Dicke, R.; Wickenkamp, R. J. Chem. Soc., Chem. Commun. 1985, 354.
14. (d) Mitchell, T. N.; Wickenkamp, R.; Amamria, A.; Dicke, R.; Schneider, U. J. Org. Chem. 1987, 52, 4868.
15. (e) Murakami, M.; Morita, Y.; Ito, Y. J. Chem. Soc., Chem. Commun. 1990, 428.
16. (f) Murakami, M.; Amii, H.; Takizawa, N.; Ito, Y. Organometallics 1993, 12, 4223.
17. (g) Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J. Am. Chem. Soc. 1994. 116, 8754.
18. (h) Casson, S.; Kocienski, P.; Reid, G.; Smith, N.; Street, J. M.; Webster, M. Synthesis 1994, 1301.
19. (i) Murakami, M.; Yoshida, T.; Kawanami, S.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 6408.
20. (j) Ito, Y.; Bando, T.; Matsuura, T.; Ishikawa, M. J. Chem. Soc., Chem. Commun. 1986, 980.
21. (k) Tsuji, Y.; Obora, Y. J. Am. Chem. Soc. 1991, 113, 9368.
22. (I) Lipshutz, B. H.; Reuter, D. C.; Ellsworth, E. L. J. Org. Chem. 1989, 54, 4975.
23. (m) Chenard, B. L.; Laganis, E. D.; Davidson, F.; RajanBabu, T. V. J. Org. Chem. 1985. 50, 3666.
24. (n) Obora, Y.; Tsuji, Y.; Asayama, M.; Kawamura, T. Organometallics 1993, 12, 4697.
25. (a) Mori, M.; Kaneta, N.; Isono, N.; Shibasaki, M. Tetrahedron Lett. 1991, 32, 6139.
26. (b) Mori, M.; Kaneta, N.; Isono, N.; Shibasaki, M. J. Orqanomet. Chem. 1993, 455, 255;
27. (c) 1994, 464, 35.
28. (d) Mori, M.; Isono, N.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1993, 58, 2972.
29. (e) Mori, M.; Hashimoto, A.; Shibasaki, M. J. Org. Chem. 1993, 58, 6503.
30. (f) Honda, T.; Mori, M. Chem. Lett. 1994, 1013.
31. (g) Sato, H.; Isono, N.; Okamura, K.; Date, T.; Mori, M. Tetrahedron Lett. 1994, 35, 2035.
32. (h) Kinoshita, A.; Mori, M. Chem. Lett. 1994, 1475.
33. (i) Isono, N.; Mori, M. J. Org. Chem. 1995, 60, 115.
34. (j) Isono, N.; Mori, M. Tetrahedron Lett. 1995, 36, 9345.
35. (k) Isono, N.; Mori, M. Main Group Met. Chem. 1996, 19, 277.
36. (l) Sato, H.; Isono, N.; Miyoshi, I.; Mori, M. Tetrahedron 1996, 52, 8143.
37. (m) Isono, N.; Mori, M. J. Org. Chem. 1996, 61, 7867.
38. Stannyl anion prepared from organotin halides: (a) Kuivila, H. G.; Considine, J. L.; Kennedy, J. D. J. Am. Chem. Soc. 1972, 94, 7206.
39. (b) Kitching, W.; Olszowy, H.; Waugh, J.; Doddrel, D. J. Org. Chem. 1978, 43, 898.
40. (c) Blake, D.; Coates, G. E.; Tate, J. M. J. Chem. Soc: 1961, 618.
41. (d) Tamborsky, C.; Ford, F. E.; Lehn, W. L.; Moore, G. J.; Soloski, E. J. J. Org. Chem. 1962, 27, 619.
42. (e) Tamborsky, C.; Ford, F. E.; Soloski, E. J. J. Org. Chem. 1963, 28, 181. Stannyl anion prepared from hexaorganoditins:
43. (f) Still, W. C. J. Am. Chem. Soc. 1977, 99, 4836.
44. (g) J. Am. Chem. Soc. 1978, 100, 1481.
45. (h) Quintard, J. P.; Hauvette-Frey, S.; Pereyre, M. Bull. Soc. Chim. Belg. 1978, 87, 505. Stannyl anion prepared from organotin hydrides:
46. (i) Corriu, R. J. P.; Guerin, C. J. Organomet. Chem. 1980, 197, C19.
47. (a) Grob, C. A.; Baumann, W. Helv. Chim. Acta 1955, 38, 594.
48. (b) Grob, C. A. Angew. Chem., Int. Ed. Engl. 1969, S, 535.
49. (c) Schreiber, S. J. Am. Chem. Soc. 1980, 102, 6163.
50. (d) Mahajan, J. R.; de Araujo, H. C. Synthesis 1981, 49.
51. 3 and CsF was used in order to convert it to the corresponding Michael addition product 13.
52. (a) San Filippo, J., Jr.; Silberman, J. J. Am. Chem. Soc. 1982, 104, 2831.
53. (b) Ashby, E. C.; DePriest, R. J. Am. Chem. Soc. 1982, 104, 6144.
54. (a) Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380.
55. (b) Mitsunobu, O. Synthesis 1981, 1.
56. (a) Ziegler, K.; Wilms, H. Justus Liebigs Ann. Chem. 1950, 567, 1.
57. (b) Cope, A. C.; Pike, R. I.; Spencer, C. F. J. Am. Chem. Soc. 1953, 75, 3212.
58. Isomerization preferably occurs with irons-18 rather than trans-19; because trans-19a was never obtained as a product from the reaction mixture, it was rationalized that, in the presence of an excess amount of stannyl anions, trans-18a first isomerizes to cis-18a, which then undergoes a conjugated addition, leading to cis-19a.
59. (a) Cope, A. C.; Ganelin, C. R.; Johnson, H. W., Jr.; Van Auken, T. V.; Winkler, J. S. J. Am. Chem. Soc. 1963, 85, 3276.
60. (b) Cope, A. C.; Mehta, A. S. J. Am. Chem. Soc. 1964, 86, 5626.
61. (c) Cope, A. C.; Pawson, B. A. J. Am. Chem. Soc. 1965, 87, 3649.
62. (d) Bach, R. D.; Mazur, U.; Hamama, I.; Lauderback, S. K. Tetrahedron 1963, 28, 1955.
63. (e) Manor, P. C.; Shoemaker, D. P.; Parkes, P. S. J. Am. Chem. Soc. 1970, 92, 5260.
64. (a) Coke, J. L.; Cooke, M. P., Jr.; Mourning, M. C. Tetrahedron Lett. 1968, 18, 2247.
65. (b) Reese, C. B.; Shaw, A. J. Am. Chem. Soc. 1970, 92, 2566.
66. (c) Whitham, G. H.; Wright, M. J. Chem, Soc. (c) 1971, 886,
67. Prior, M. J.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1986, 683.
68. (e) Vedejs, E.; Snoble, K. A. J.; Fuchs, P. L. J. Org. Chem. 1973, 38, 3561. Synthesis by photoisomerization of cis-cyclooctene:
69. (f) Swenton, J. S. J. Org. Chem. 1969, 34, 3217.
70. (g) Deyrup, J. A.; Betkouski, M. J. Org. Chem. 1972, 37, 3561.
71. (h) Inoue, Y.; Takamuku, S.; Sakurai, H. Synthesis 1977, 111.
72. (a) Corey, E. J.; Shulman, J. I. Tetrahedron Lett. 1968, 33, 3655.
73. (b) Aratani, T.; Nakanishi, Y.; Nozaki, H. Tetrahedron 1970, 26, 4339.
74. (c) Newton, P. F.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1979, 3072.
75. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357.
76. Sen, S.; Roach, S. L.; Boggs, J. K.; Ewing, G. J.; Magrat, J. J. Org. Chem. 1997, 62, 6684.
77. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.