The influence of benzylic protection and allylic substituents on the CuCl-TMEDA catalyzed rearrangement of N-allyl-N-benzyl-2,2-dihaloamides to γ-lactams. Application to the stereoselective synthesis of pilolactam

Tetrahedron

Volumn 55, Issue 18, 1999, Pages 5839-5852

  Ghelfi, Franco ^a   Bellesia, Franco ^a   Forti, Luca ^a   Ghirardini, Gianluca ^a   Grandi, Romano ^a   Libertini, Emanuela ^a   Montemaggi, Maria C ^a   Pagnoni, Ugo M ^a   Pinetti, Adriano ^a   De Buyck, Laurent ^b   Parsons, Andrew F ^c  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^b GHENT UNIVERSITY   (Belgium)

^c UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Cyclisation; Lactams; Pyrrolidinones; Radicals and radical reactions

Indexed keywords

AMIDE; GAMMA LACTAM DERIVATIVE; N ALLYL N BENZYL 2,2 DIHALOAMIDE; PILOLACTAM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CHOLINERGIC STIMULATION; CYCLIZATION; DIASTEREOISOMER; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0033617231     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00247-1     Document Type: Article

References (31)

1. 1. Benedetti, M.; Forti, L., Ghelfi, F.; Pagnoni, U. M.; Ronzoni, R. Tetrahedron 1997, 41, 14031.
2. 2. Baldovini, N.; Bertrand, M.-P.; Carrière, A.; Nouguier, R.; Plancher, J.-M. J. Org. Chem. 1996, 61, 3205.
3. 3. Nagashima, H.; Ozaki, N; Ishii, M.; Seki, K.; Washiyama, M.; Itoh, K. J. Org. Chem. 1993, 58, 464.
4. 4. Jasperse, C. P.; Curran, D. P.; Fevig T. L. Chem. Rev. 1991, 91, 1237.
5. 5. Rachita, M. A.; Slough, G. A. Tetrahedron Lett. 1993, 34, 6821.
6. 6. Nagashima, H.; Wakamatsu, H.; Ozaki, N.; Ishii, T.; Watanabe, M.; Tajima, T.; Itoh, K. J. Org. Chem. 1992, 57, 1682.
7. 7. Bellesia, F.; Boni, M.; Ghelfi, F.; Pagnoni, U. M. Tetrahedron Lett. 1994, 35, 2961.
8. 8. De Buyck, L.; Casaert, F.; De Lepeleire, C.; Schamp, N. Bull. Soc. Chim. Belg. 1988, 97, 525.
9. 9. Cheikh, R. B.; Chaabouni, R.; Laurent, A.; Mison, P.; Nafti, A. Synthesis 1983, 685.
10. 10. Dolby, L. J.; Fedorouk, N. A.; Esfandiari, S.; Garst, M. E. US U. S. 5,675,019 (C.A. 1997, 127, 307539).
11. 11. WoldeMussie, E.; Ruiz, G.; Chen, J. Investigative Ophthalmology & Visual Science 1995, 36, S718.
12. 12. WoldeMussie, E.; Ruiz, G. Investigative Ophthalmology & Visual Science 1995, 36, S718.
13. 13. Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746.
14. nd ed., Wiley, New York, 1991, 364-366.
15. 15. Baker, S. R.; Parsons, A. F ; Wilson, M. Tetrahedron Lett. 1998, 39, 331.
16. 16. Chapman, D. T.; Crout, D. H. G.; Mahmoudian, M; Scopes, D. I. C.; Smith, P. W. J. Chem. Soc., Chem. Commun. 1996, 2415.
17. 17. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, VCH, Weinheim, 1996.
18. 18. Belvisi, L.; Gennari C.; Poli G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945.
19. 19. Cardillo, B.; Galeazzi, R.; Mobbili, G; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663.
20. 20. Baussane, I.; Royer, J. Tetrahedron Lett. 1998, 39, 845.
21. 21. Prochilo N. Riarrangiamento di N-allil-α, α-dicloroammidi, β-o γ-funzionalizzate, a 2-pirrolidinoni analoghi sostituiti dell'acido γ-amminobutirrico, Univ. degli Studi di Modena, Modena (Italy), 1998.
22. 22. Rigaudy, J.; Klesney, S. P. Nomenclature of Organic Chemistry. Pergamon Press, Oxford, 1979, 478.
23. 23. Parsons, A. F.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. I 1994, 1945.
24. 24. Naito, T.; Honda, Y.; Bhavakul, V.; Yamaguchi, S.; Fujiwara, A.; Miyata, O.; Ninomiya, I. Chem. Pharm. Bull. 1997, 45, 1932.
25. 25. Moppet, C. E.; Sutherland, J. K. J. Chem. Soc. (C) 1968, 3040.
26. 26. Criegge, R.; Hover, H. Chem. Ber. 1960, 93, 2521.
27. 27. Ince, J.; Ross, T. M.; Shipman, M.; Slawin, A. M. Z. Tetrahedron 1996, 52, 7037.
28. 28. Guy, A.; Barbetti, J. F. Synth. Commun. 1992, 22, 853.
29. 29. Overman, L. E. J. Am. Chem. Soc. 1976, 98, 2901.
30. 30. Sato, T.; Wada, Y.; Nishimoto, M.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans I 1989, 879.
31. 31. Stork, G.; Clarke, F. H. J. Am. Chem. Soc. 1961, 83, 3114.