Michael-Stork addition of cyclopentyl enamine to allenyl ketones and esters

Journal of Organic Chemistry

Volumn 70, Issue 20, 2005, Pages 8239-8241

  Silvestri, Maximilian A ^a   Bromfield, Deborah C ^a   Lepore, Salvatore D ^a  

^a FLORIDA ATLANTIC UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; CYCLOPENTANE DERIVATIVE; ENAMINE; ESTER DERIVATIVE; KETONE DERIVATIVE;

ADDITION REACTION; ARTICLE; ISOMERIZATION; MICHAEL STORK ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; REACTION ANALYSIS; REACTION OPTIMIZATION; SUBSTITUTION REACTION;

CYCLOPENTANES; ESTERS; INDICATORS AND REAGENTS; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRIDINES;

EID: 25444513192     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0512103     Document Type: Article

References (20)

1. (a) Lepore, S. D.; He, Y. J.; Damisse, P. J. Org. Chem. 2004, 69, 9171.
2. (b) Lepore, S. D.; He, Y. J. J. Org. Chem. 2005, 70, 4546.
3. (a) Franck-Neumann, M.; Brion, F. Angew. Chem., Int. Ed. Engl. 1979, 18, 688.
4. (b) Franck-Neumann, M.; Martina, D.; Neff, D. Tetrahedron: Asymmetry 1998, 9, 697.
5. (c) Franck-Neumann, M.; Neff, D.; Nouali, H.; Martina, D.; de Cian, A. Synlett 1994, 657.
6. Lepore, S. D.; Khoram, A.; Bromfield, D. C.; Cohen, P.; Jairaj, V.; Silvestri, M. A. J Org. Chem. 2005, 70, 7443.
7. Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16.
8. Nishide, K.; Ichihashi, S.; Kimura, H.; Katoh, T.; Node, M. Tetrahedron Lett. 2001, 42, 9237.
9. (a) Machida, S.; Hashimoto, Y.; Saigo, K.; Inoue, J. Y.; Hasegawa, M. Tetrahedron 1991, 47, 3737.
10. (b) Hall, H. K. Jr.; Abdelkader, M.; Glogowski, M. E. J. Org. Chem. 1982, 47, 3691.
11. (c) Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207.
12. Epsztajn, J.; Bieniek, A.; Brzezinski, J. Z. Pol. J. Chem. 1980, 54, 341.
13. (a) Weichert, A.; Hoffman, H. M. R. J. Org. Chem. 1991, 56, 4098.
14. (b) Xu, Y.; Dolbier, W. R., Jr. J. Org. Chem. 1997, 62, 6503.
15. Schreiber, S. L.; Meyers, H. V.; Wiberg, K. B. J. Am. Chem. Soc. 1986, 108, 8274.
16. (a) Jorgensen, K. A. Eur. J. Org. Chem. 2004, 2093.
17. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498.
18. (a) Nenajdenko, V. J.; Druzhinin, S. V.; Balenkova, E. S. Russ. Chem. Bull., Int. Ed. 2004, 53, 435.
19. (b) Andrew, R. J.; Mellor, J. M.; Reid, G. Tetrahedron 2000, 56, 7255.
20. Barluenga, J.; Ballesteros, A.; Bernadro de la Rua, R.; Santamaria, J.; Rubio, E.; Tomas, M. J. Am. Chem. Soc. 2003, 125, 1834.