Nickel-catalyzed cyclizations of alkynyl enones with concomitant stereoselective tri- or tetrasubstituted alkene introduction

Journal of the American Chemical Society

Volumn 118, Issue 8, 1996, Pages 2099-2100

  Montgomery, John ^a   Savchenko, Alexey V ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CYCLOALKANE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029987180     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952026+     Document Type: Article

References (41)

1. For representative examples, see: (a) Petrier, C.; de Souza Barbosa, J. C.; Dupuy, C.; Luche, J. L. J. Org. Chem. 1985, 50, 5761. (b) Schwartz, J ; Carr, D. B.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053. (c) Schwartz, J.; Loots, M. J.; Kosugi, H. J. Am. Chem. Soc. 1980, 102, 1333.
2. For representative examples, see: (a) Petrier, C.; de Souza Barbosa, J. C.; Dupuy, C.; Luche, J. L. J. Org. Chem. 1985, 50, 5761. (b) Schwartz, J ; Carr, D. B.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053. (c) Schwartz, J.; Loots, M. J.; Kosugi, H. J. Am. Chem. Soc. 1980, 102, 1333.
3. For representative examples, see: (a) Petrier, C.; de Souza Barbosa, J. C.; Dupuy, C.; Luche, J. L. J. Org. Chem. 1985, 50, 5761. (b) Schwartz, J ; Carr, D. B.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053. (c) Schwartz, J.; Loots, M. J.; Kosugi, H. J. Am. Chem. Soc. 1980, 102, 1333.
4. (a) Johnson, J. R.; Tully, P. S.; Mackenzie, P. B.; Sabat, M. J. Am. Chem. Soc. 1991, 113, 6172.
5. (b) Grisso, B. A.; Johnson, J. R.; Mackenzie, P. B. J. Am. Chem. Soc: 1992, 114, 5160.
6. (a) Dayrit, F. M.; Gladkowski, D. E.; Schwartz, J. J. Am. Chem. Soc. 1980, 102, 3976.
7. (b) Daynt, F. M.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4466.
8. The existence of copper-enone d-π* complexes as intermediates in cuprate additions to enones is fairly well established, but the sequence of events leading from the d-π* complex to products is controversial. For d-π* complex characterization, see: Vellekoop. A. S.; Smith, R. A. J. J. Am. Chem. Soc. 1994, 116, 2902 and references therein.
9. For examples of intermolecular insertion of an enone-derived nickel π-allyl intermediate to an alkyne. see: (a) Ikeda, S.; Sato, Y. J. Am. Chem. Soc 1994, 116, 5975. (b) After submission of this manuscript, a related process involving dimethylzinc was reported. Ikeda, S.; Yamamoto, H.; Kondo, K.; Sato, Y. Organometallics 1995, 14, 5015.
10. For examples of intermolecular insertion of an enone-derived nickel π-allyl intermediate to an alkyne. see: (a) Ikeda, S.; Sato, Y. J. Am. Chem. Soc 1994, 116, 5975. (b) After submission of this manuscript, a related process involving dimethylzinc was reported. Ikeda, S.; Yamamoto, H.; Kondo, K.; Sato, Y. Organometallics 1995, 14, 5015.
11. For leading references to alkenyl Inflate-, alkenyl iodide-, and alkyne-initiated palladium-catalyzed cyclization processes, see: (a) Sugihara, T.; Copéret, C.; Owczarczyk, Z.; Harring, L. S.; Negishi, E. J. Am. Chem. Soc. 1994, 116, 7923. (b) Overman, L. E. Pure. Appl. Chem. 1994, 66, 1423. (c) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421.
12. For leading references to alkenyl Inflate-, alkenyl iodide-, and alkyne-initiated palladium-catalyzed cyclization processes, see: (a) Sugihara, T.; Copéret, C.; Owczarczyk, Z.; Harring, L. S.; Negishi, E. J. Am. Chem. Soc. 1994, 116, 7923. (b) Overman, L. E. Pure. Appl. Chem. 1994, 66, 1423. (c) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421.
13. For leading references to alkenyl Inflate-, alkenyl iodide-, and alkyne-initiated palladium-catalyzed cyclization processes, see: (a) Sugihara, T.; Copéret, C.; Owczarczyk, Z.; Harring, L. S.; Negishi, E. J. Am. Chem. Soc. 1994, 116, 7923. (b) Overman, L. E. Pure. Appl. Chem. 1994, 66, 1423. (c) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421.
14. For examples of nickel-promoted cyclization reactions initiated by alkyl or alkenyl halides. see: (a) Knochel, P. Synlett 1995, 393. (b) Solé, D.; Cancho, Y.: Llebaria, A.; Moretó, J. M.; Delgado, A. J. Am. Chem. Soc 1994, 116, 12133.
15. For examples of nickel-promoted cyclization reactions initiated by alkyl or alkenyl halides. see: (a) Knochel, P. Synlett 1995, 393. (b) Solé, D.; Cancho, Y.: Llebaria, A.; Moretó, J. M.; Delgado, A. J. Am. Chem. Soc 1994, 116, 12133.
16. 3-hybridized functionality bearing β-hydrogens. see: Trost, B. M.; Pfrengle, W.; Urabe. H.; Dumas, J. J. Am. Chem. Soc: 1992, 114, 1923.
17. Carbometalation/capture sequences beginning with oxidative addition of palladium(0) to vinyl iodides and inflates are well documented, but to our knowledge, no examples that tolerate β-hydrogens in the transmetalating agent have been reported. For representative examples, see: (a) Negishi, E. Pure Appl. Chem. 1992, 64, 323. (b) Brown, A., Grigg, R., Ravishankar, T.: Thornton-Pett, M Tetrahedron Lett 1994, 35, 2753.
18. Carbometalation/capture sequences beginning with oxidative addition of palladium(0) to vinyl iodides and inflates are well documented, but to our knowledge, no examples that tolerate β-hydrogens in the transmetalating agent have been reported. For representative examples, see: (a) Negishi, E. Pure Appl. Chem. 1992, 64, 323. (b) Brown, A., Grigg, R., Ravishankar, T.: Thornton-Pett, M Tetrahedron Lett 1994, 35, 2753.
19. We use the term "cyclization with alkylation" for processes that introduce a carbon substituent and "reductive cyclization" for processes that introduce hydrogen at the reduced sites. For leading references to reductive cyclizations involving other metals and different substrate classes, see: (a) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785 (b) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc 1995, 117. 6787. (c) Trost, B M , Rise, F. J. Am. Chem. Soc 1987, 109, 3161.
20. We use the term "cyclization with alkylation" for processes that introduce a carbon substituent and "reductive cyclization" for processes that introduce hydrogen at the reduced sites. For leading references to reductive cyclizations involving other metals and different substrate classes, see: (a) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785 (b) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc 1995, 117. 6787. (c) Trost, B M , Rise, F. J. Am. Chem. Soc 1987, 109, 3161.
21. We use the term "cyclization with alkylation" for processes that introduce a carbon substituent and "reductive cyclization" for processes that introduce hydrogen at the reduced sites. For leading references to reductive cyclizations involving other metals and different substrate classes, see: (a) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785 (b) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc 1995, 117. 6787. (c) Trost, B M , Rise, F. J. Am. Chem. Soc 1987, 109, 3161.
22. For nickel-catalyzed cycloisomerizations of related substrates without reduction, see: Trost, B M., Tour, J M. J Am. Chem. Soc. 1987, 109, 5268.
23. 1H NMR) at the alkenyl position was observed.
24. (a) Yamamoto, T.; Yamamoto, A.; Ikeda, S. J. Am. Chem. Soc: 1971, 93, 3350.
25. (b) Kurosawa, H.; Emoto, M.; Ohnishi, H.; Miki. K.; Kasai, N.; Tatsumi, K.; Nakamura, A. J. Am. Chem. Soc. 1987, 109, 6333.
26. (c) Temple, J. S.; Riediker, M.; Schwartz, J. J. Am. Chem. Soc. 1982, 104, 1310.
27. (d) Sustmann, R.; Lau, J.; Zipp, M. Tetrahedron Lett. 1986, 27, 5207.
28. (e) Binger, P.; Doyle, M. J. J. Organomet. Chem. 1978, 162, 195.
29. Reductive elimination of aryl(alkyl)nickel(II) complexes was reported to be accelerated by electron transfer. In the absence of electrontransfer agents, reductive elimination occurred too slowly to be important in the nickel-catalyzed coupling of aryl halides and alkylmetals. Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc: 1975, 97, 7262.
30. For a discussion of the effect of phosphine structure on the relative rates of reductive elimination and β-hydride elimination, see: (a) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158. (b) Kumada, M. Pure Appl. Chem. 1980, 52, 669.
31. For a discussion of the effect of phosphine structure on the relative rates of reductive elimination and β-hydride elimination, see: (a) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158. (b) Kumada, M. Pure Appl. Chem. 1980, 52, 669.
32. We thank a referee for suggesting this possibility.
33. For organometallic approaches, see: (a) Bronk, B. S.; Lippard, S. J.; Danheiser, R. L. Organometallics 1993, 12, 3340. (b) Wender, P. A.; White, A. W. J. Am. Chem. Soc. 1988, 110, 2218.
34. For organometallic approaches, see: (a) Bronk, B. S.; Lippard, S. J.; Danheiser, R. L. Organometallics 1993, 12, 3340. (b) Wender, P. A.; White, A. W. J. Am. Chem. Soc. 1988, 110, 2218.
35. (c) Cooke, M. P J Org. Chem. 1992, 57, 1495.
36. For related radical approaches, see: (a) Stork, G.; Mook, R. J. Am Chem. Soc. 1987, 109, 2829. (b) Middleton, D. S.; Simpkins, N. S Tetrahedron 1990, 46, 545. (c) Marinovic, N. N.; Ramanathan, H. Tetrahedron Lett. 1983, 24, 1871. (d) Bhaskar, K. V.; Subba Rao, G S. R. Tetrahedron Lett. 1989, 30, 225. (e) Janardhanam, S.: Shanmugam, P.; Rajagopalan, K. J. Org Chem. 1993, 58, 7782.
37. For related radical approaches, see: (a) Stork, G.; Mook, R. J. Am Chem. Soc. 1987, 109, 2829. (b) Middleton, D. S.; Simpkins, N. S Tetrahedron 1990, 46, 545. (c) Marinovic, N. N.; Ramanathan, H. Tetrahedron Lett. 1983, 24, 1871. (d) Bhaskar, K. V.; Subba Rao, G S. R. Tetrahedron Lett. 1989, 30, 225. (e) Janardhanam, S.: Shanmugam, P.; Rajagopalan, K. J. Org Chem. 1993, 58, 7782.
38. For related radical approaches, see: (a) Stork, G.; Mook, R. J. Am Chem. Soc. 1987, 109, 2829. (b) Middleton, D. S.; Simpkins, N. S Tetrahedron 1990, 46, 545. (c) Marinovic, N. N.; Ramanathan, H. Tetrahedron Lett. 1983, 24, 1871. (d) Bhaskar, K. V.; Subba Rao, G S. R. Tetrahedron Lett. 1989, 30, 225. (e) Janardhanam, S.: Shanmugam, P.; Rajagopalan, K. J. Org Chem. 1993, 58, 7782.
39. For related radical approaches, see: (a) Stork, G.; Mook, R. J. Am Chem. Soc. 1987, 109, 2829. (b) Middleton, D. S.; Simpkins, N. S Tetrahedron 1990, 46, 545. (c) Marinovic, N. N.; Ramanathan, H. Tetrahedron Lett. 1983, 24, 1871. (d) Bhaskar, K. V.; Subba Rao, G S. R. Tetrahedron Lett. 1989, 30, 225. (e) Janardhanam, S.: Shanmugam, P.; Rajagopalan, K. J. Org Chem. 1993, 58, 7782.
40. For related radical approaches, see: (a) Stork, G.; Mook, R. J. Am Chem. Soc. 1987, 109, 2829. (b) Middleton, D. S.; Simpkins, N. S Tetrahedron 1990, 46, 545. (c) Marinovic, N. N.; Ramanathan, H. Tetrahedron Lett. 1983, 24, 1871. (d) Bhaskar, K. V.; Subba Rao, G S. R. Tetrahedron Lett. 1989, 30, 225. (e) Janardhanam, S.: Shanmugam, P.; Rajagopalan, K. J. Org Chem. 1993, 58, 7782.
41. Our initial studies have shown that intermolecular three-component couplings are successful. Montgomery. J.; Savchenko, A. V.; Chui, H. Abstracts of Papers, 210th ACS National Meeting, Chicago, IL. August 24, 1995: American Chemical Society: Washington, DC. 1995; ORGN 415.