Organozinc/nickel(0)-promoted cyclizations of bis-enones

Journal of Organic Chemistry

Volumn 61, Issue 5, 1996, Pages 1562-1563

  Savchenko, Alexey V ^a   Montgomery, John ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000757165     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960166b     Document Type: Article

References (33)

1. Montgomery, J.; Savchenko, A. V. J. Am. Chem. Soc. 1996, 118, in press.
2. Montgomery, J.; Savchenko, A. V.; Zhao, Y. J. Org. Chem. 1995, 60, 5699.
3. For related tandem Michael additions using other classes of nucleophiles, see: (a) Klimko, P. G.; Singleton, D. A. Synthesis 1994, 979. (b) Shida, N.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1992, 57, 5049. (c) Saito, S.; Hirohara, Y. Narahara, O. Moriwake T. J. Am. Chem. Soc. 1989, 111, 4533. (d) Yoshii, E.; Hori, K.; Nomura, K.; Yamaguchi, K. Synlett 1995, 568 and references therein.
4. For related tandem Michael additions using other classes of nucleophiles, see: (a) Klimko, P. G.; Singleton, D. A. Synthesis 1994, 979. (b) Shida, N.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1992, 57, 5049. (c) Saito, S.; Hirohara, Y. Narahara, O. Moriwake T. J. Am. Chem. Soc. 1989, 111, 4533. (d) Yoshii, E.; Hori, K.; Nomura, K.; Yamaguchi, K. Synlett 1995, 568 and references therein.
5. For related tandem Michael additions using other classes of nucleophiles, see: (a) Klimko, P. G.; Singleton, D. A. Synthesis 1994, 979. (b) Shida, N.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1992, 57, 5049. (c) Saito, S.; Hirohara, Y. Narahara, O. Moriwake T. J. Am. Chem. Soc. 1989, 111, 4533. (d) Yoshii, E.; Hori, K.; Nomura, K.; Yamaguchi, K. Synlett 1995, 568 and references therein.
6. For related tandem Michael additions using other classes of nucleophiles, see: (a) Klimko, P. G.; Singleton, D. A. Synthesis 1994, 979. (b) Shida, N.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1992, 57, 5049. (c) Saito, S.; Hirohara, Y. Narahara, O. Moriwake T. J. Am. Chem. Soc. 1989, 111, 4533. (d) Yoshii, E.; Hori, K.; Nomura, K.; Yamaguchi, K. Synlett 1995, 568 and references therein.
7. For representative examples of nickel-promoted conjugate additions, see: (a) Petrier, C.; de Souza Barbosa, J. C.; Dupuy, C.; Luche, J. L. J. Org. Chem. 1985, 50, 5761. (b) Smith, A. B., III; Leenay, T. L. J. Am. Chem. Soc. 1989, 111, 5761. (c) Schwartz, J.; Carr, D. B.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053. (d) Schwartz, J.; Loots, M. J.; Kosugi, H. J. Am. Chem. Soc. 1980, 102, 1333. (e) Flemming, S.; Kabbara, J.; Nickisch, K.; Neh, H.; Westermann, J. Tetrahedron Lett. 1994, 35, 6075.
8. For representative examples of nickel-promoted conjugate additions, see: (a) Petrier, C.; de Souza Barbosa, J. C.; Dupuy, C.; Luche, J. L. J. Org. Chem. 1985, 50, 5761. (b) Smith, A. B., III; Leenay, T. L. J. Am. Chem. Soc. 1989, 111, 5761. (c) Schwartz, J.; Carr, D. B.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053. (d) Schwartz, J.; Loots, M. J.; Kosugi, H. J. Am. Chem. Soc. 1980, 102, 1333. (e) Flemming, S.; Kabbara, J.; Nickisch, K.; Neh, H.; Westermann, J. Tetrahedron Lett. 1994, 35, 6075.
9. For representative examples of nickel-promoted conjugate additions, see: (a) Petrier, C.; de Souza Barbosa, J. C.; Dupuy, C.; Luche, J. L. J. Org. Chem. 1985, 50, 5761. (b) Smith, A. B., III; Leenay, T. L. J. Am. Chem. Soc. 1989, 111, 5761. (c) Schwartz, J.; Carr, D. B.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053. (d) Schwartz, J.; Loots, M. J.; Kosugi, H. J. Am. Chem. Soc. 1980, 102, 1333. (e) Flemming, S.; Kabbara, J.; Nickisch, K.; Neh, H.; Westermann, J. Tetrahedron Lett. 1994, 35, 6075.
10. For representative examples of nickel-promoted conjugate additions, see: (a) Petrier, C.; de Souza Barbosa, J. C.; Dupuy, C.; Luche, J. L. J. Org. Chem. 1985, 50, 5761. (b) Smith, A. B., III; Leenay, T. L. J. Am. Chem. Soc. 1989, 111, 5761. (c) Schwartz, J.; Carr, D. B.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053. (d) Schwartz, J.; Loots, M. J.; Kosugi, H. J. Am. Chem. Soc. 1980, 102, 1333. (e) Flemming, S.; Kabbara, J.; Nickisch, K.; Neh, H.; Westermann, J. Tetrahedron Lett. 1994, 35, 6075.
11. For representative examples of nickel-promoted conjugate additions, see: (a) Petrier, C.; de Souza Barbosa, J. C.; Dupuy, C.; Luche, J. L. J. Org. Chem. 1985, 50, 5761. (b) Smith, A. B., III; Leenay, T. L. J. Am. Chem. Soc. 1989, 111, 5761. (c) Schwartz, J.; Carr, D. B.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053. (d) Schwartz, J.; Loots, M. J.; Kosugi, H. J. Am. Chem. Soc. 1980, 102, 1333. (e) Flemming, S.; Kabbara, J.; Nickisch, K.; Neh, H.; Westermann, J. Tetrahedron Lett. 1994, 35, 6075.
12. 13C NMR data identical to 4a was previously reported (see ref 7d). The author has deposited atomic coordinates for 4a with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
13. More complete studies to understand the factors that control stereochemistry are under investigation. Elegant studies by several investigators in related zirconium-catalyzed cyclomagnesiations of dienes demonstrated that cis/trans diastereoselectivities were dependent upon numerous factors including magnesium reagent structure. (a) Knight, K. S.; Wang, D.; Waymouth, R. M. Ziller, J. J. Am. Chem. Soc 1994, 116, 1845. (b) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc 1991, 113, 6268. (c) Taber, D. F.; Louey, J. P.; Wang, Y.; Nugent, W. A.; Dixon, D. A.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 9457. (d) Takahashi, T.; Seki, T.; Nitto, Y.; Saburi, M.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266. (e) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097.
14. More complete studies to understand the factors that control stereochemistry are under investigation. Elegant studies by several investigators in related zirconium-catalyzed cyclomagnesiations of dienes demonstrated that cis/trans diastereoselectivities were dependent upon numerous factors including magnesium reagent structure. (a) Knight, K. S.; Wang, D.; Waymouth, R. M. Ziller, J. J. Am. Chem. Soc 1994, 116, 1845. (b) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc 1991, 113, 6268. (c) Taber, D. F.; Louey, J. P.; Wang, Y.; Nugent, W. A.; Dixon, D. A.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 9457. (d) Takahashi, T.; Seki, T.; Nitto, Y.; Saburi, M.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266. (e) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097.
15. More complete studies to understand the factors that control stereochemistry are under investigation. Elegant studies by several investigators in related zirconium-catalyzed cyclomagnesiations of dienes demonstrated that cis/trans diastereoselectivities were dependent upon numerous factors including magnesium reagent structure. (a) Knight, K. S.; Wang, D.; Waymouth, R. M. Ziller, J. J. Am. Chem. Soc 1994, 116, 1845. (b) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc 1991, 113, 6268. (c) Taber, D. F.; Louey, J. P.; Wang, Y.; Nugent, W. A.; Dixon, D. A.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 9457. (d) Takahashi, T.; Seki, T.; Nitto, Y.; Saburi, M.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266. (e) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097.
16. More complete studies to understand the factors that control stereochemistry are under investigation. Elegant studies by several investigators in related zirconium-catalyzed cyclomagnesiations of dienes demonstrated that cis/trans diastereoselectivities were dependent upon numerous factors including magnesium reagent structure. (a) Knight, K. S.; Wang, D.; Waymouth, R. M. Ziller, J. J. Am. Chem. Soc 1994, 116, 1845. (b) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc 1991, 113, 6268. (c) Taber, D. F.; Louey, J. P.; Wang, Y.; Nugent, W. A.; Dixon, D. A.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 9457. (d) Takahashi, T.; Seki, T.; Nitto, Y.; Saburi, M.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266. (e) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097.
17. More complete studies to understand the factors that control stereochemistry are under investigation. Elegant studies by several investigators in related zirconium-catalyzed cyclomagnesiations of dienes demonstrated that cis/trans diastereoselectivities were dependent upon numerous factors including magnesium reagent structure. (a) Knight, K. S.; Wang, D.; Waymouth, R. M. Ziller, J. J. Am. Chem. Soc 1994, 116, 1845. (b) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc 1991, 113, 6268. (c) Taber, D. F.; Louey, J. P.; Wang, Y.; Nugent, W. A.; Dixon, D. A.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 9457. (d) Takahashi, T.; Seki, T.; Nitto, Y.; Saburi, M.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266. (e) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097.
18. (a) Enholm, E. J.; Kinter, K. S. J. Org. Chem. 1995, 60, 4850.
19. (b) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784.
20. Fu recently reported a radical cyclization procedure that is catalytic in tributyltin hydride: Hays, D S.; Fu, G. C. J. Org. Chem. 1996, 61, 4. (d) Taniguchi, Y.; Kusudo, T.; Beppu, F.; Makioka, Y.; Takaki, K.; Fujiwara, Y. J. Chem. Soc. Jpn. 1994, 62. (e) Chavan, S. P.; Ethiraj, K. S. Tetrahedron Lett. 1995, 36, 2281. (f) Schobert, R.; Maaref, F.; Dürr, S. Synlett 1995, 83.
21. Fu recently reported a radical cyclization procedure that is catalytic in tributyltin hydride: Hays, D S.; Fu, G. C. J. Org. Chem. 1996, 61, 4. (d) Taniguchi, Y.; Kusudo, T.; Beppu, F.; Makioka, Y.; Takaki, K.; Fujiwara, Y. J. Chem. Soc. Jpn. 1994, 62. (e) Chavan, S. P.; Ethiraj, K. S. Tetrahedron Lett. 1995, 36, 2281. (f) Schobert, R.; Maaref, F.; Dürr, S. Synlett 1995, 83.
22. Fu recently reported a radical cyclization procedure that is catalytic in tributyltin hydride: Hays, D S.; Fu, G. C. J. Org. Chem. 1996, 61, 4. (d) Taniguchi, Y.; Kusudo, T.; Beppu, F.; Makioka, Y.; Takaki, K.; Fujiwara, Y. J. Chem. Soc. Jpn. 1994, 62. (e) Chavan, S. P.; Ethiraj, K. S. Tetrahedron Lett. 1995, 36, 2281. (f) Schobert, R.; Maaref, F.; Dürr, S. Synlett 1995, 83.
23. Fu recently reported a radical cyclization procedure that is catalytic in tributyltin hydride: Hays, D S.; Fu, G. C. J. Org. Chem. 1996, 61, 4. (d) Taniguchi, Y.; Kusudo, T.; Beppu, F.; Makioka, Y.; Takaki, K.; Fujiwara, Y. J. Chem. Soc. Jpn. 1994, 62. (e) Chavan, S. P.; Ethiraj, K. S. Tetrahedron Lett. 1995, 36, 2281. (f) Schobert, R.; Maaref, F.; Dürr, S. Synlett 1995, 83.
24. These conjugate additions are considerably slower than additions to enones lacking the pentenyl side chain. Ziegler, F. E.; Wallace, O. B. J. Org. Chem. 1995, 60, 3626.
25. The relative stereochemical relationship about the bond connecting the bicyclooctane and cyclohexane moieties of 10 was arbitrarily assigned.
26. (a) Johnson, J. R.; Tully, P. S.; Mackenzie, P. B.; Sabat, M. J. Am. Chem. Soc. 1991, 113, 6172.
27. (b) Grisso, B. A.; Johnson, J. R.; Mackenzie, P. B. J. Am. Chem. Soc. 1992, 114, 5160.
28. Evidence in support of oxidative addition of a catalytically-active Ni(I) species to enones by a mechanism involving single electron transfer has been provided. Dayrit, F. M.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4466.
29. Stille, J. K. Angew. Chem., Int. Ed. Engl 1986, 25, 508.
30. (a) Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975.
31. (b) Ikeda, S.; Yamamoto, H.; Kondo, K.; Sato, Y. Organometallics 1995, 14, 5015.
32. The latter of these two sequences would be required in cyclizations involving dimethylzinc (eq 5).
33. A mechanism involving the oxidative cychzation of a nickel(0)/ bis-enone complex to a metallacyclopentane intermediate (as in related zirconium-catalyzed reactions, ref 6) cannot be ruled out. However, given that 2a is formed from diphenylzinc. we favor the mechanism described in Scheme 1. A mechanism involving a radical cyclization also cannot be ruled out. However, the dependence on organozinc structure is more easily explained by the mechanism depicted in Scheme 1.