Experimental studies of Lewis acid catalyzed additions of long chained alcohols to activated 1,4-benzoquinone

Tetrahedron

Volumn 54, Issue 9, 1998, Pages 1943-1952

  Hormi, Osmo E O ^a   Moilanen, Anu M ^a  

^a UNIVERSITY OF OULU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE DERIVATIVE; ALCOHOL DERIVATIVE; REAGENT;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032567952     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10409-4     Document Type: Article

References (57)

1. 1. a) Harden, R. C.; Hodgkinson, T. J.; McKillop, A.; Prowse, W. G.; Urquhart, W. J. Tetrahedron 1997, 55, 21.
2. b) Martín, R.; Pascual, O.; Romea, P.; Rovira, R.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1997, 38, 1633.
3. c) Engler, T. A.; Meduna, S. P.; LaTessa, K. O.; Chai, W. J. Org. Chem. 1996, 61, 8598.
4. d) Engler, T. A.; Chai, W.; LaTessa, K. O. J. Org. Chem. 1996, 61, 9297.
5. e) Engler, T. A.; Ali, M. H.; Takusagawa, F. J. Org. Chem. 1996, 61, 8456.
6. f) Lipshutz, B. H.; James, B.; Vance, S. Carrico, I. Tetrahedron Lett. 1997, 38, 753.
7. g) DiMare, M. J. Org. Chem. 1996, 61, 8378.
8. h) Casarrubios, L.; Pérez, J. A.; Brookhart, M.; Templeton, J. L. J. Org. Chem. 1996, 61, 8358.
9. i) Kita, Y.; Kitagaki, S.; Yoshida, Y.; Mihara, S.; Fang, D-F.; Fujioka, H. Tetrahedron Lett. 1997, 38, 1061.
10. j) Sato, M.; Aoyagi, S.; Yago, S.; Kibayashi, C. Tetrahedron Lett. 1996, 37, 9063.
11. k) Jain, N. F.; Takenaka, N.; Panek, J. S. J. Am. Chem. Soc. 1996, 118, 12475.
12. l) Hu, Q-S.; Vitharana, D.; Zheng, X-F.; Wu, C.; Kwan, C. M. S.; Pu, L. J. Org. Chem. 1996, 61, 8370.
13. m) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela A. J. Tetrahedron 1996, 52, 2167.
14. n) Yamabe, S.; Dai, T.; Minato, T. J. Am. Chem Soc. 1995, 117, 10994 and references therein
15. 2. a) Santelli, M., Pons, J-M., Lewis Acids and Selectivity in Organic Synthesis; CRC Press, New York, 1996.
16. b) Shambayati, S.; Schreiber, S.L. Lewis Acid Carbonyl Complexation in Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press, Oxford, 1991, 283.
17. c) Denmark, S. E.; Almstead, N. G. J. Am. Chem Soc. 1993, 115, 3133 and references therein
18. 3. Farina, F.; Valderrama, J. Synthesis 1971, 315
19. 4. a) De Labbey, A.; Baudry, A.; Bauer, D.; Bore, P. Eur. Pat.Appl. EP 376,776.
20. b) Baudry, A.; Junino, A.; Richard, H. Eur. Pat.Appl. EP 460,996.
21. c) Farina, F.; Valderrama, J. An. Quim. 1974, 70(3), 258.
22. d) Inoue, Y.; Morita, T.; Kitajima, H. Nippon Kagaku Kaishi 1996, 2, 160.
23. e) Cassis, R.; Fernandez, M.; Tapia, R.; Valderrama, V. A. Synth.Commun. 1987, 77(9), 1077.
24. f) Müller, P.; Venakis. T.; Eugster, C. H. Helv. Chim. Acta 1979, 62, 2350.
25. g) Farina, F.; Valderrama, J. An. Quim. 1976, 72(11-12), 902.
26. h) Fumagalli, S. E.; Eugster, C. H. Helv. Chim. Acta 1971, 54, 959.
27. i) Engler, T. A.; Combrink, K. D.; Tagusakawa, F. J. Chem. Soc., Chem. Commun. 1989, 1573.
28. j) Engler, T. A.; Letavic, M. A.; Combrink, K. D.; Tagusakawa, F. J. Org. Chem. 1990, 55, 5810.
29. k) Engler, T. A.; Reddy, J. P.; Combrink, K. D.; Vander Velde, D. J. Org. Chem. 1990, 55, 1248.
30. l) Uno, H. J. Org. Chem. 1986, 51, 350.
31. 5. The manuscript is in progress.
32. 6. a) Prager, B., Jacobson, D., Schmidt, P., Stern, D. Beilstein Handbuch der Organichen Chemie, vierte auflage, Band X, Verlag von Julius Springer, Berlin, 1927, 386.
33. b) Ulrich, H., Richter, R.20in Methoden der Organichen Chemie (Hauben Weyl), Grundmann, C.(ed), Georg Thieme, Stuttgart, 1977, vol.VII/3a pp. 44-46 and references therein
34. 7. Aranda, G., Fetizon, M. Synthesis 1975, 330-332
35. 8. Rozeboom, M.D., Tegmo-Larsson, I-M., Houk, K. N. J. Org. Chem. 1981, 46, 2338-2345
36. 9. Naruta, Y; Uno, H.; Maruyama, K. Tetrahedron Lett. 1981, 22, 5221
37. 3. Cabral, J.; Laszlo, P.; Mahé, L. Tetrahedron Lett. 1989, 30, 3969.
38. b) Childs, R. F.; Mulholland, D. L.; Nixon, A. Can. J. Chem. 1982, 60, 801
39. 11. a) Kuturev, A. A.; Moskva, V. V. Russian Chemical Reviews 1991, 60(1), 72.
40. b) Hormi, O. E. O.; Moilanen A. M. PCT /FI96/00047
41. 12. We used two distinct approaches to select the suitable LAs to the experiments. In one of the approaches, because the donor atoms of carbomethoxyquinones are hard Lewis base oxygen atoms, we thought that tighter and more stable complexes are formed between carbonyl oxygens and hard LAs. a) Laszlo, P.; Teston, M. J. Am. Chem Soc. 1990, 112, 8750.
42. b) Carlson, R.; Lundstedt, T.; Nordahl, Å; Prochazka, M. Acta Chem. Scand. 1986, B 40, 522.
43. c) Braddock, D. C.; Brown, J. M.; Guiry, P. J. J. Chem. Soc., Chem. Commun. 1993, 1244) On the other hand, as mentioned earlier enhancement of reactivity of the carbonyl groups can be achieved through a nonchelated or a chelated intermediate. A suitable example in this connection is the investigation of Chen et al.,
44. d) Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem Soc. 1992, 114, 1778, who compared the transition state energies of LAs and alkoxy ketones in chelated and nonchelated 1:1 complexes. They showed that complexation enhances the reactivity of the ketone and, furthermore, the chelated intermediate lowers the the transition state energy further and, thus, increases the reaction rate. The chelation restricts also bond rotation and increases stereoselectivity. Their results gave us a hint of promise on that a bidentate chelating metal could further diminished LUMO energy of the β-carbon and give an additional activation towards oxygen nucleophiles.
45. 13. (equation presented)
46. 14. a) Keck, G. E.; Castellino, S. J. Am. Chem Soc. 1986, 108, 3847,
47. b) PhD thesis, Letavic, M. A. University of Kansas, 1992, Diss. Abstr. Int. B. 1993, 54(4), 1969
48. c) PhD thesis, Reddy, J. P. M. University of Kansas, 1991, Diss. Abstr. Int. B 1993, 54(1), 252
49. 15. (equation presented)
50. 16. a) Mulzer, J; Pointner, A.; Straßer, R; Hoyer, K.; Nagel, U. Tetrahedron Lett. 1995, 36, 3679.
51. b) Wang, S.; Howe, G. P.; Mahal, R. S.; Procter, G. Tetrahedron Lett. 1992, 33, 3351.
52. c) Keck, G. E.; Dougherty, S. M.; Savin, K. A. J. Am. Chem Soc. 1995, 117, 6210.
53. d) Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem 1994, 59, 7889
54. 17. Unidentified polar addition products, which remained on the baseline in t.l.c. analysis.
55. 18. (equation presented)
56. 2 can be used as a catalyst in the reaction between inactivated quinone and long chained alcohols. We found that the catalyst did work also in this case, but only in 10 % yield. (Hormi, O. E. O.; Moilanen, A. M. unpublished results)
57. 19. When the decarbomethoxylation was carried out with 2-carbomethoxy-3-benzyloxyHQ (6f) using the same reaction conditions, only tarry material was produced.