Cyclization of δ,ε-acetylenic amines and aminoacids into cyclic enamines. A very efficient and simple access to polysubstituted pyrrolidines

Tetrahedron Letters

Volumn 38, Issue 15, 1997, Pages 2677-2680

  Cossy, J ^a   Belotti, D ^a   Bellosta, V ^a   Boggio, C ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030943454     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00452-8     Document Type: Article

References (16)

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2. b) Natural Occuring Pyrrolizidine Alkaloids; Rizk, A.-F. M., Ed; CRC: Boston, 1991.
3. c) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Am. Chem. Soc. 1996, 118, 8266-8277 and references therein.
4. General references : a) Chekulaeva, I. A.; Kondrat'eva, L. V. Russ. Chem. Rev. 1965, 34, 669-680.
5. b) Gibson, M. S. The Chemistry of the Amino Group; S. Patai, Ed.; Interscience: New York, 1968, 61-65.
6. c) Chailis, B. C.; Butler, A. R. ibid. 1968, 292.
7. d) Suminov, S. I.; Kost, A. N. Russ. Chem. Rev. 1969, 38, 884-899.
8. e) Jäger, V.; Viehe, H. G. Houben-Weyl, Methoden der Organishen Chemie; Thieme Verlag: Stuttgart, 1977, Vol. 5/2a, 713-724.
9. f) March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons: New York, 1992, 768-770 and references therein.
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11. b) Pez, G. P.; Galle, J. E. Pure Appl. Chem. 1985, 57, 1917-1926
12. Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295-9306, and references therein.
13. Tokuda, M.; Fujita, H.; Suginome, H. Tetrahedron Lett. 1990, 31, 5353-5356.
14. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849-3862.
15. Compounds 18-22 were obtained pure by heating compounds 13-17 without any solvent under an argon atmosphere.
16. Dose, K. Chem. Ber. 1957, 1251