β-Ketoesters derived from pyroglutamic acid: New entry to hydroxylated pyrrolizidinones

Heterocycles

Volumn 75, Issue 10, 2008, Pages 2541-2547

  Le Bouc, Géraldine ^a   Thomassigny, Christine ^a   Greck, Christine ^a  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79751483538     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-08-11418     Document Type: Article

References (23)

1. For recent publications, see: a) E. Dietrich and W. D. Lubell, J. Org. Chem., 2003, 68, 6988.
2. F. M. Cordero, F. Pisaneschi, K. M. Batista, S. Valenza, F. Machetti, and A. Brandi, J. Org. Chem., 2005, 70, 856.
3. M. H. V. Ramana Rao, E. Pinyol, and W. D. Lubell, J. Org. Chem., 2007, 72, 736.
4. As exemples, see: a) D. A. Burnett, J.-K. Choi, D. J. Hart, and Y.-M. Tsai, J. Am. Chem. Soc., 1984, 106, 8201.
5. H. Takahata, Y. Banba, and T. Momose, Tetrahedron, 1991, 47, 7635.
6. X. L. M. Despinoy and H. McNab, Tetrahedron, 2000, 56, 6359.
7. For the synthesis of 4-(R)-hydroxy-L-pyroglutamic acid, see: a) T. Ohta, A. Hosoi, and S. Nozoe, Tetrahedron Lett., 1988, 29, 329.
8. A. G. Avent, A. N. Bowler, P. M. Doyle, C. M. Marchand, and D. W. Young, Tetrahedron Lett., 1992, 33, 1509.
9. D. W. Brooks, L. D. L. Lu, and S. Masamune, Angew. Chem., Int. Ed. Engl, 1979, 1, 72.
10. a) J. P. Genêt, V. Ratovelomanana-Vidal, C. Caño de Andrade, X. Pfister, P. Guerreiro, and J. Y. Lenoir, Tetrahedron Lett, 1995, 36, 4801.
11. V. Ratovelomanana-Vidal and J. P. Genêt, Organomet. Chem., 1998, 567, 163.
12. a) C. Thomassigny and C. Greck, Tetrahedron: Asymmetry, 2004, 15, 199.
13. C. Thomassigny, M. T. Barroso, and C. Greck, Letters Org. Chem., 2005, 316.
14. G. Le Bouc, C. Thomassigny, and C. Greck, Tetrahedron: Asymmetry, 2006, 17, 2006.
15. The catalyst was prepared under argon according to the next procedure: To bis-(2-methylallyl)-cycloocta-1, 5-diene-ruthenium (II) complex (0.02 equiv.) and (R) - or (S)-2, 2'-bis (diphenylphosphino)-1, 1'-binaphtyl (0.02 equiv.) in degazed acetone (1 mL/mmol of catalyst) was added a methanolic solution of hydrogen bromide (0.15-0.18M 0.04 equiv.). The reaction mixture was stirred 30 min. The solvents were evaporated and the P-ketoester (1 mmol) in freshly distilled degazed MeOH (1.7 mL) was cannulated to the catalyst. The reaction mixture was stirred under hydrogen atmosphere (see tables for conditions of pressure, temperature and time). The solvents were evaporated and a purification by column chromatography gave the corresponding P-hydroxyesters.
16. 3)}.
17. +: 278.1552; found: 278.1556.
18. a) T. Ikariya, Y. Ishii, H. Kawano, T. Arai, M. Saburi, S. Yoshikawa, and S. Akutagawa, J. Chem. Soc., Chem. Commun., 1985, 922.
19. H. Kawano, T. Ikariya, Y. Ishii, M. Saburi, S. Yoshikawa, Y. Uchida, and H. Kumobayashi, J. Chem. Soc., Perkin Trans. 1, 1989, 1571.
20. K. Mashima, T. Nakamura, Y. Matsuo, and K. Tani, J. Organomet. Chem., 2000, 607, 51.
21. N. Ohtake, H. Jona, S. Okada, O. Okamoto, Y. Imai, R. Ushijima, and S. Nakagawa, Tetrahedron: Asymmetry, 1997, 8, 2939.
22. +: 336.1971; found: 336.1969.
23. +: 336.1971; found: 336.1977.