Efficient synthesis of 3-methylene-2-pyrrolidinone and highly exoselective diels-alder addition to cyclopentadiene

Tetrahedron Letters

Volumn 40, Issue 5, 1999, Pages 867-870

  Fotiadu, Frédéric ^a   Pardigon, Olivier ^a   Buono, Gérard ^a   Le Corre, Maurice ^b   Hercouët, Alain ^b  

^a Ecole Centrale Marseille   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; 3 METHYLENE 2 PYRROLIDONONE; CYCLOPENTADIENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

BETULACEAE;

EID: 0033613709     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02542-8     Document Type: Article

References (12)

1. (a) Fotiadu, F.; Archavlis, A.; Buono, G. Tetrahedron Lett. 1990, 31, 4859-4862.
2. (b) Fotiadu, F.; Michel, F.; Buono, G. Tetrahedron Lett. 1990, 31, 4863-4866.
3. (c) Roush, W. R.; Brown, B. B. J. Org. Chem. 1992, 57, 3380-3387 and references therein.
4. Kamata, S.; Okada, T.; Shioda, T.; Haga, N.; Hamada, Y.; Matsumoto, S. Jpn. Kokai Tokkyo Koho JP 05,339,232 [93,339,232] (Cl. C07D207 / 36), 21 Dec 1993, Appl. 92 / 176,097, 09 Jun 1992; 9 pp. (CA 120, 1994, 244659j).
5. Klutchko, S.; Hoefle, M. L.; Smith, R. D.; Essenburg, A. D.; Parker, R. B.; Nemeth, V. L.; Ryan, M. J.; Dugan, D. H.; Kaplan, H. R. J. Med. Chem. 1981, 24, 104-109.
6. 3 106-108 °C].
7. Najer, H.; Chabrier, P.; Giudicelli, R. Bull. Soc. Chim. France 1959, 611-614.
8. P-C = 72.0 Hz), 23.36, 14.65.
9. Jouglet, B.; Oumoch, S.; Rousseau, G. Synth. Commun. 1995, 25, 3869-3874.
10. 1H NOESY NMR experiments. The endo epimer 8n exhibited a nuclear Overhauser effect between the methylene group of the pyrrolidone ring in exo position and the proton of the methylene bridge facing it, whereas the exo adduct 8x lacked this effect.
11. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
12. Adam, W.; Hassemann, L. Tetrahedron Lett. 1991, 32, 7033-7036.