Synthesis of N-Protected 3,3-Difluoroazetidin-2-ones

Synthesis

Volumn , Issue 16, 2003, Pages 2483-2486

  Lacroix, Simon ^a   Cheguillaume, Arnaud ^a   Gérard, Stéphane ^a   Marchand Brynaert, Jacqueline ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Cyclization; Cycloaddition; Fluoroazetidinone; Reformatsky type reaction

Indexed keywords

ADDITION REACTIONS; BROMINE COMPOUNDS; DERIVATIVES; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); ZINC COMPOUNDS;

CYCLIZATION; CYCLOADDITION;

ORGANIC COMPOUNDS;

ACETIC ACID DERIVATIVE; AZETIDINONE DERIVATIVE; BENZHYDRYL DERIVATIVE; PROPIONIC ACID DERIVATIVE; SCHIFF BASE; TRIAZINE DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CYCLIZATION; CYCLOADDITION; REFORMATSKY REACTION; SYNTHESIS;

EID: 0344874099     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42415     Document Type: Article

References (27)

1. Filler, R.; Kobayashi, Y.; Yagupolskii, L. M. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Elsevier: Amsterdam, 1993.
2. Kukhar, V. P.; Soloshonok, V. A. Fluorine-Containing Amino Acids. Synthesis and Properties; Wiley: Chichester, 1995.
3. Kitazume, T.; Yamazaki, T. Experimental Methods in Organic Fluorine Chemistry; Gordon and Breach: Kodansha Tokyo, 1998.
4. Taguchi, T.; Kitagawa, O.; Suda, Y.; Ohkawa, S.; Hashimoto, A.; Iitaka, Y.; Kobayashi, Y. Tetrahedron Lett. 1988, 29, 5291.
5. Baldwin, J. E.; Lynch, G. P.; Schofield, C. J. Tetrahedron 1992, 48, 9085.
6. Angelastro, M. R.; Bey, P.; Mehdi, S.; Peet, N. P. Bioorg. Med. Chem. Lett. 1992, 2, 1235.
7. Marcotte, S.; Pannecoucke, X.; Feasson, C.; Quirion, J. C. J. Org. Chem. 1999, 64, 8461.
8. Thaisrivongs, S.; Schostarez, H. J.; Pals, D. T.; Turner, S. R. J. Med. Chem. 1987, 30, 1837.
9. Iseki, K.; Kuroki, Y.; Asada, D.; Takahoshi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 10271.
10. Nakayama, K.; Kawato, H. C.; Inagaki, H.; Nakajima, R.; Kitamura, A.; Someya, K.; Ohta, T. Org. Lett. 2000, 2, 977.
11. Otaka, A.; Watanabe, H.; Mitsuyama, E.; Yukimasa, A.; Tamamura, H.; Fuji, N. Tetrahedron Lett. 2001, 42, 285.
12. Joyeau, R.; Molines, H.; Labia, R.; Wakselman, M. J. Med. Chem. 1988, 31, 370.
13. Wakselman, M.; Joyeau, R.; Kobaiter, R.; Bogetto, N.; Vergely, I.; Maillard, J.; Okochi, V.; Montagne, J.-J.; Reboud-Ravaux, M. FEBS Lett. 1991, 282, 377.
14. Vergely, I.; Bogetto, N.; Okochi, V.; Golpayegani, S.; Reboud-Ravaux, M. ; Kobaiter, R.; Joyeau, R.; Wakselman, M. Eur. J. Med. Chem. 1995, 30, 199.
15. Cheguillaume, A.; Lacroix, S.; Marchand-Brynaert, J. Tetrahedron Lett. 2003, 43, 2375.
16. Kocienski, P. J. Protecting Groups, 2nd ed.; Thieme: Stuttgart, 2000.
17. Laurent, M.; Belmans, M.; Kemps, L.; Cérésiat, M.; Marchand-Brynaert, J. Synthesis 2003, 570.
18. Shiozaki, M.; Masuko, H. Heterocycles 1984, 22, 1727.
19. Rivera, A.; Torres, O. L.; Jesus, D.; Morales-Rios, M. S.; Joseph-Nathan, P. Synth. Commun. 2002, 32, 1407.
20. Steere, J. A.; Sampson, P. B.; Honek, J. F. Bioorg. Med. Chem. Lett. 2002, 12, 457.
21. Kobayashi, S.; Iiomori, T.; Izawa, T.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 2406.
22. Huang, H.; Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1984, 1465.
23. Murayama, T.; Kobayashi, T.; Miura, T. Tetrahedron Lett. 1995, 36, 3703.
24. Ogilvie, W. W.; Yoakim, C.; Dô, F.; Haché, B.; Lagacé, L.; Naud, J.; O'Meara, J. A.; Déziel, R. Bioorg. Med. Chem. 1999, 7, 1521.
25. Katritzky, A. R.; Rachwal, S.; Rachwal, B. J. Chem. Soc., Perkin Trans. 1 1987, 799.
26. Katritzky, A. R.; Nichols, D. A.; Qi, M. Tetrahedron Lett. 1998, 39, 7063.
27. Gérard, S.; Nollet, G.; Vande Put, J.; Marchand-Brynaert, J. Bioorg. Med. Chem. 2002, 10, 3955.