A short asymmetric synthesis of 4,4-disubstituted-γ-butyrolactones from racemic 2-methylcyclohexanone in multigram scale

Tetrahedron Asymmetry

Volumn 9, Issue 12, 1998, Pages 2031-2034

  Pinheiro, Sergio ^a   De Farias, Florence M C ^a   Saraiva, Analúcia S ^a   Campos, Marcos P A ^a  

^a FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; GAMMA BUTYROLACTONE DERIVATIVE;

ARTICLE; ENANTIOMER; PRIORITY JOURNAL; RACEMIC MIXTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032547029     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00173-6     Document Type: Article

References (46)

1. (a) Chamberlin, A. R.; Dezube, M.; Reich, S. H.; Sall, D. J. J. Am. Chem. Soc. 1989, 111, 6247.
2. (b) Stork, G.; Paterson, I.; Lee, F. K. C. J. Am. Chem. Soc. 1982, 104, 4686.
3. (c) Wrobel, J. E.; Ganem, B. J. Org. Chem. 1983, 48, 3761.
4. (d) Meinwald, J.; Huang, J. J. Am. Chem. Soc. 1981, 103, 861.
5. (e) Corey, E. J.; Myers, A. G.; Takahashi, N.; Yamane, H.; Schraudolf, H. Tetrahedron Lett. 1986, 27, 5083.
6. (f) Mori, K.; Ebata, T.; Takechi, S. Tetrahedron 1984, 60, 1761.
7. Maga, J. A. Critical Rev. Fd. Sci. Nut. 1976, 8, 1.
8. Petterson, T.; Eklund, A.-M.; Wahlberg, I. J. Agric. Food Chem. 1993, 41, 2097.
9. (a) Fang, J.-M.; Hong, B.-L.; Liao, L.-F. J. Org. Chem. 1987, 52, 855.
10. (b) Clerici, A.; Porta, O.; Zago, P. Tetrahedron 1986, 42, 561.
11. (c) Hope, D.; Brönneke, A. Tetrahedron Lett. 1983, 1687.
12. (d) Fukuzawa, S.; Nakanishi, A.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commun. 1986, 624.
13. (e) Petragnani, N.; Ferraz, H. M. C.; Silva, G. V. J. Synthesis 1986, 157.
14. (f) Corey, E. J.; Mitra, R. B.; Uda, H. J. Am. Chem. Soc. 1964, 86, 485.
15. (g) Imamura, P. M.; Santiago, G. M. P. Synth. Commun. 1997, 27, 2479.
16. (h) El Ali, B.; Alper, H. J. Org. Chem. 1991, 56, 5357.
17. (i) Albinati, A.; Bravo, P; Ganazzoli, F.; Resnati, G.; Viani, F. J. Chem. Soc., Perkin Trans. 1 1986, 1405.
18. (j) Bloch, R.; Brillet, C. Tetrahedron: Asymmetry 1991, 2, 797.
19. (k) Corey, E. J.; Zheng, G. Z. Tetrahedron Lett. 1997, 38, 2045.
20. (a) Doyle, M. P.; van Oeveren, A.; Westrum, L. J.; Protopopova, M. N.; Clayton Jr., T. W. J. Am. Chem. Soc. 1991, 113, 8982 and references cited therein.
21. (b) Rodríguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461.
22. (c) Yu, W.-Y.; Bensimon, C.; Alper, H. Chem. Eur. J. 1997, 3, 417.
23. (d) Tamai, Y.; Akiyama, M.; Okamura, A.; Miyano, S. J. Chem. Soc. Chem. Commun. 1992, 687.
24. (e) Maio, G. D.; Tranfo, G.; Vecchi, E.; Zeuli, E. Gazz. Chim. Ital. 1983, 113, 173.
25. (f) Ancliff, R. A.; Russel, A. T.; Sanderson, A. J. Tetrahedron: Asymmetry 1997, 8, 3379.
26. (a) Costa, P. R. R.; Pinheiro, S.; Lopes, C. C. Tetrahedron Lett. 1985, 26, 4155.
27. (b) Pinheiro, S.; Castro, R. N.; Fernandes, M. F. G.; Costa, P. R. R. Synth. Commun. 1991, 21, 703.
28. (a) d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459.
29. (b) d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Trends Org. Chem. 1993, 4, 555.
30. (c) Cavé, C.; Daley, V.; d'Angelo, J.; Guingant, A. Tetrahedron: Asymmetry 1995, 6, 79.
31. (d) Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795.
32. (e) Pfau, M.; Revial, G.; Guingant, A.; d'Angelo, J. J. Am. Chem. Soc. 1985, 107, 273.
33. (a) Pinheiro, S.; Saraiva, A. S.; Campos, M. P. A. J. Braz. Chem. Soc. 1996, 7, 353.
34. (b) Narasaka, K.; Sakakura, T.; Uchimaru, T.; Guédin-Vuong, D. J. Am. Chem. Soc. 1984, 106, 2954.
35. (a) Krow, G. R. Org. React. 1993, 43, 251.
36. (b) Desmaële, D.; d'Angelo, J. Tetrahedron Lett. 1989, 30, 345.
37. (c) Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415.
38. (d) Sato, T.; Maeno, H.; Noro, T.; Fujisawa, T. Chem. Lett. 1988, 1739.
39. Desmaële, D.; Mekouar, K.; d'Angelo, J. J. Org. Chem. 1997, 62, 3890.
40. Costa, P. R. R.; Castro, R. N.; Farias, F. M. C.; Bergter, L.; Antunes, O. A. C. Tetrahedron: Asymmetry 1993, 4, 1499.
41. (a) Ambroise, L.; Chassagnard, C.; Revial, G.; d'Angelo, J. Tetrahedron: Asymmetry 1991, 2, 407.
42. (b) Matsuyama, H.; Ebisawa, Y.; Kobayashi, M.; Kamigata, N. Heterocycles 1989, 29, 449.
43. (c) Desmaële, D.; d'Angelo, J.; Bois, C. Tetrahedron: Asymmetry 1990, 1, 759.
44. (a) Guingant, A.; Hammami, H. Tetrahedron: Asymmetry 1991, 2, 411.
45. (b) Brünner, H.; Kraus, J.; Lautenschlager, H. J. Monatshefte für Chemie 1988, 119, 1161.
46. (c) d'Angelo, J.; Guingant, A.; Riche, C.; Chiaroni, A. Tetrahedron Lett. 1988, 29, 2667.