Cobalt-Mediated Aldol-Type Reactions

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 1159-1163

  Orsini, Fulvia ^a  

^a Dipto di Chim Organ e Industriale   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001162972     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961905r     Document Type: Article

References (23)

1. Orsini, F.; Pelizzoni F.; Pulici, M.; Vallarino, L. M. J. Org. Chem. 1994, 59, 1-3.
2. Orsini F.; Pulici, M.; Vallarino. L. M. J. Organomet. Chem. 1995, 495, C1-C5.
3. Orsini, F.; Pulici, M. Highlights on Recent Advancement on Reformatsky-Type Reactions: the Cobalt Approach. In Trends in Organometallic Chemistry; Research Trends Ed.; Trivandrum, India, 1994; Vol. 1, pp 625-667.
4. (a) Klein, H. F. Angew. Chem. 1971, 83, 363.
5. (b) Klein, H. F.; Karsch, H. H. Chem Ber. 1975, 108, 944-955.
6. The species formed from Co(II) by reduction with magnesium metal in the presence of 4 equiv of triphenylphosphine was not isolated. The course of the reduction with magnesium and of the addition to carbonyl compounds suggests the formation of a Co(0) species. However, for correcteness, we will refer to it as a low-state-oxidation complex.
7. 3 angle.
8. Preparation of the magnesium enolate from various 2-bromo-2-alkyl-5,5′-dimethylcyclopentanones and α-bromo-α'-tert-butyl ketones in ether-benzene solutions at reflux, followed by condensation with carbonyl compounds was reported: Fellmann, P; Dubois, J. E. Tetrahedron 1978, 34, 1349-1357.
9. A 1:1:0.5 organic reagents/Co ratio was also tested and produced a ∼ 50% recovery of starting product.
10. The enolate structure was unambigously assigned for some magnesium derivatives: Fellmann, P; Dubois, J. E. Tetrahedron Lett. 1977, 247-250.
11. Mukayama, T. Org. React. 1982, 28, 203-331.
12. For aldol-type reactions based on oxidative metalation of the halo carbonyl compounds, see the following for examples, (a) Titanium: Ishihara, T.; Yamanaka, T.; Ando, T. Chem. Lett. 1984, 1165-1168. (b) Chromium: Dubois, J. E.; Axiotis, G.; Bertounesque, E. Tetrahedron Lett. 1985, 26, 4371-4372. (c) Boron: Nozaki, K.; Oshima K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1041-1044. (d) Aluminum: Matsubara, S.; Tsuboriwa, N; Morizava, Y.; Oshima K.; Nozaki, H. Bull. Soc. Chim. Jpn. 1984, 57, 3243-3246. (e) Tin: Mukaiyama, T.; Harada, T. Chem. Lett. 1982, 161-164; Kato, J. I.; Mukaiyama, T. Chem. Lett. 1983, 1727-1728. (f) Antimony: Huang, Y. Z.; Chen C.; Shen, Y. J. Chem. Soc., Perkin Trans. 1988, 1, 2855-2859. (g) Cerium: Fukuzawa, S.; Sumimoto, N.; Fijinama, T.; Sakai, S. J. Org. Chem. 1990, 55, 1628-1631.
13. For aldol-type reactions based on oxidative metalation of the halo carbonyl compounds, see the following for examples, (a) Titanium: Ishihara, T.; Yamanaka, T.; Ando, T. Chem. Lett. 1984, 1165-1168. (b) Chromium: Dubois, J. E.; Axiotis, G.; Bertounesque, E. Tetrahedron Lett. 1985, 26, 4371-4372. (c) Boron: Nozaki, K.; Oshima K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1041-1044. (d) Aluminum: Matsubara, S.; Tsuboriwa, N; Morizava, Y.; Oshima K.; Nozaki, H. Bull. Soc. Chim. Jpn. 1984, 57, 3243-3246. (e) Tin: Mukaiyama, T.; Harada, T. Chem. Lett. 1982, 161-164; Kato, J. I.; Mukaiyama, T. Chem. Lett. 1983, 1727-1728. (f) Antimony: Huang, Y. Z.; Chen C.; Shen, Y. J. Chem. Soc., Perkin Trans. 1988, 1, 2855-2859. (g) Cerium: Fukuzawa, S.; Sumimoto, N.; Fijinama, T.; Sakai, S. J. Org. Chem. 1990, 55, 1628-1631.
14. For aldol-type reactions based on oxidative metalation of the halo carbonyl compounds, see the following for examples, (a) Titanium: Ishihara, T.; Yamanaka, T.; Ando, T. Chem. Lett. 1984, 1165-1168. (b) Chromium: Dubois, J. E.; Axiotis, G.; Bertounesque, E. Tetrahedron Lett. 1985, 26, 4371-4372. (c) Boron: Nozaki, K.; Oshima K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1041-1044. (d) Aluminum: Matsubara, S.; Tsuboriwa, N; Morizava, Y.; Oshima K.; Nozaki, H. Bull. Soc. Chim. Jpn. 1984, 57, 3243-3246. (e) Tin: Mukaiyama, T.; Harada, T. Chem. Lett. 1982, 161-164; Kato, J. I.; Mukaiyama, T. Chem. Lett. 1983, 1727-1728. (f) Antimony: Huang, Y. Z.; Chen C.; Shen, Y. J. Chem. Soc., Perkin Trans. 1988, 1, 2855-2859. (g) Cerium: Fukuzawa, S.; Sumimoto, N.; Fijinama, T.; Sakai, S. J. Org. Chem. 1990, 55, 1628-1631.
15. For aldol-type reactions based on oxidative metalation of the halo carbonyl compounds, see the following for examples, (a) Titanium: Ishihara, T.; Yamanaka, T.; Ando, T. Chem. Lett. 1984, 1165-1168. (b) Chromium: Dubois, J. E.; Axiotis, G.; Bertounesque, E. Tetrahedron Lett. 1985, 26, 4371-4372. (c) Boron: Nozaki, K.; Oshima K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1041-1044. (d) Aluminum: Matsubara, S.; Tsuboriwa, N; Morizava, Y.; Oshima K.; Nozaki, H. Bull. Soc. Chim. Jpn. 1984, 57, 3243-3246. (e) Tin: Mukaiyama, T.; Harada, T. Chem. Lett. 1982, 161-164; Kato, J. I.; Mukaiyama, T. Chem. Lett. 1983, 1727-1728. (f) Antimony: Huang, Y. Z.; Chen C.; Shen, Y. J. Chem. Soc., Perkin Trans. 1988, 1, 2855-2859. (g) Cerium: Fukuzawa, S.; Sumimoto, N.; Fijinama, T.; Sakai, S. J. Org. Chem. 1990, 55, 1628-1631.
16. For aldol-type reactions based on oxidative metalation of the halo carbonyl compounds, see the following for examples, (a) Titanium: Ishihara, T.; Yamanaka, T.; Ando, T. Chem. Lett. 1984, 1165-1168. (b) Chromium: Dubois, J. E.; Axiotis, G.; Bertounesque, E. Tetrahedron Lett. 1985, 26, 4371-4372. (c) Boron: Nozaki, K.; Oshima K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1041-1044. (d) Aluminum: Matsubara, S.; Tsuboriwa, N; Morizava, Y.; Oshima K.; Nozaki, H. Bull. Soc. Chim. Jpn. 1984, 57, 3243-3246. (e) Tin: Mukaiyama, T.; Harada, T. Chem. Lett. 1982, 161-164; Kato, J. I.; Mukaiyama, T. Chem. Lett. 1983, 1727-1728. (f) Antimony: Huang, Y. Z.; Chen C.; Shen, Y. J. Chem. Soc., Perkin Trans. 1988, 1, 2855-2859. (g) Cerium: Fukuzawa, S.; Sumimoto, N.; Fijinama, T.; Sakai, S. J. Org. Chem. 1990, 55, 1628-1631.
17. For aldol-type reactions based on oxidative metalation of the halo carbonyl compounds, see the following for examples, (a) Titanium: Ishihara, T.; Yamanaka, T.; Ando, T. Chem. Lett. 1984, 1165-1168. (b) Chromium: Dubois, J. E.; Axiotis, G.; Bertounesque, E. Tetrahedron Lett. 1985, 26, 4371-4372. (c) Boron: Nozaki, K.; Oshima K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1041-1044. (d) Aluminum: Matsubara, S.; Tsuboriwa, N; Morizava, Y.; Oshima K.; Nozaki, H. Bull. Soc. Chim. Jpn. 1984, 57, 3243-3246. (e) Tin: Mukaiyama, T.; Harada, T. Chem. Lett. 1982, 161-164; Kato, J. I.; Mukaiyama, T. Chem. Lett. 1983, 1727-1728. (f) Antimony: Huang, Y. Z.; Chen C.; Shen, Y. J. Chem. Soc., Perkin Trans. 1988, 1, 2855-2859. (g) Cerium: Fukuzawa, S.; Sumimoto, N.; Fijinama, T.; Sakai, S. J. Org. Chem. 1990, 55, 1628-1631.
18. For aldol-type reactions based on oxidative metalation of the halo carbonyl compounds, see the following for examples, (a) Titanium: Ishihara, T.; Yamanaka, T.; Ando, T. Chem. Lett. 1984, 1165-1168. (b) Chromium: Dubois, J. E.; Axiotis, G.; Bertounesque, E. Tetrahedron Lett. 1985, 26, 4371-4372. (c) Boron: Nozaki, K.; Oshima K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1041-1044. (d) Aluminum: Matsubara, S.; Tsuboriwa, N; Morizava, Y.; Oshima K.; Nozaki, H. Bull. Soc. Chim. Jpn. 1984, 57, 3243-3246. (e) Tin: Mukaiyama, T.; Harada, T. Chem. Lett. 1982, 161-164; Kato, J. I.; Mukaiyama, T. Chem. Lett. 1983, 1727-1728. (f) Antimony: Huang, Y. Z.; Chen C.; Shen, Y. J. Chem. Soc., Perkin Trans. 1988, 1, 2855-2859. (g) Cerium: Fukuzawa, S.; Sumimoto, N.; Fijinama, T.; Sakai, S. J. Org. Chem. 1990, 55, 1628-1631.
19. For aldol-type reactions based on oxidative metalation of the halo carbonyl compounds, see the following for examples, (a) Titanium: Ishihara, T.; Yamanaka, T.; Ando, T. Chem. Lett. 1984, 1165-1168. (b) Chromium: Dubois, J. E.; Axiotis, G.; Bertounesque, E. Tetrahedron Lett. 1985, 26, 4371-4372. (c) Boron: Nozaki, K.; Oshima K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1041-1044. (d) Aluminum: Matsubara, S.; Tsuboriwa, N; Morizava, Y.; Oshima K.; Nozaki, H. Bull. Soc. Chim. Jpn. 1984, 57, 3243-3246. (e) Tin: Mukaiyama, T.; Harada, T. Chem. Lett. 1982, 161-164; Kato, J. I.; Mukaiyama, T. Chem. Lett. 1983, 1727-1728. (f) Antimony: Huang, Y. Z.; Chen C.; Shen, Y. J. Chem. Soc., Perkin Trans. 1988, 1, 2855-2859. (g) Cerium: Fukuzawa, S.; Sumimoto, N.; Fijinama, T.; Sakai, S. J. Org. Chem. 1990, 55, 1628-1631.
20. Complexes of Co(II) acetate with 2,2′-bipyridine were reported to promote aldol condensation of aldehydes with ketones in DMF at 80 °C for several hours to give α,β-unsaturated ketones: Irie, K; Watanabe K. I. Bull. Chem. Soc. Jpn. 1980, 53, 1366-1371.
21. In one run the reaction of α-bromopropiophenone and benzaldehyde was performed in absolute tetrahydrofuran (0 °C, 1 h) and afforded 86% of the expected aldol (91/9 threo/erythro diastereoisomeric ratio).
22. House H. O.; Crumrine D. S.; Teranishi A. Y.; Olmstead H. D. J. Am. Chem. Soc. 1973, 95, 3310-3324.
23. Heathcock, C. H.; Pirrung, M. C.; Sohn, J. E. J. Org. Chem. 1979, 44, 4294-4299.