Metal-Promoted Variants of the Passerini Reaction Leading to Functionalized Heterocycles

Organic Letters

Volumn 4, Issue 9, 2002, Pages 1631-1634

  Xia, Qian ^a   Ganem, Bruce ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; HETEROCYCLIC COMPOUND; METAL;

ARTICLE; CATALYSIS; CHEMISTRY; KINETICS; SYNTHESIS;

CATALYSIS; HETEROCYCLIC COMPOUNDS; INDICATORS AND REAGENTS; KINETICS; METALS;

EID: 0037007745     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025877c     Document Type: Article

References (20)

1. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
2. Hagedorn, I.; Eholzer, U. Chem. Ber. 1965, 98, 936-940.
3. 3-etherate: (a) Müller, E.; Zeeh, B. Liebigs Ann. Chem. 1968, 715, 47-51.
4. (b) Müller, E.; Zeeh, B. Liebigs Ann. Chem. 1966, 696, 72-80.
5. 4: (a) Carofiglio, T.; Cozzi, P. G.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 2726-2736.
6. (b) Seebach, D.; Adam, G.; Gees, T.; Schiess, M.; Weigand, W. Chem. Ber. 1988, 121, 507-517.
7. Semple, J. E.; Owens, T. D.; Nguyen, K.; Levy, O. E. Org. Lett. 2000, 2, 2769-2772.
8. Tempest, P.; Ma, V.; Thomas, S.; Hua, Z.; Kelly, M. G.; Hulme, C. Tetrahedron Lett. 2001, 42, 4959-4962.
9. (a) Susaki, H.; Higashi, K. Chem. Pharm. Bull. 1992, 40, 2019-2022.
10. (b) Susaki, H.; Higashi, K. Chem. Pharm. Bull. 1993, 41, 201-204.
11. (c) Susaki, H. Chem. Pharm. Bull. 1994, 42, 1917-1918.
12. A related mechanism has been proposed for the cyclization of α-ketoimidoyl chlorides to 2-acyl-5-ethoxyoxazoles: Huang, W.-S.; Zhang, Y.-X.; Yuan, C.-Y. Synth. Commun. 1996, 26, 1149-1154.
13. (a) Sun, X.; Janvier, P.; Zhao, G.; Bienaymé, H.; Zhu, J. Org. Lett. 2001, 3, 877-880.
14. (b) Janvier, P.; Sun, X.; Bienaymé, H.; Zhu, J. J. Am. Chem. Soc. 2002, 124, 2560-2567.
15. (a) Tadesse, S.; Balan, C.; Jones, W.; Viswanadhan, V.; Hulme, C. Abstracts of Papers, 223rd National Meeting of the American Chemical Society, Orlando, FL, April 7-11, 2002; American Chemical Society: Washington, DC, 2002; ORGN-241.
16. (b) Banfi, L.; Guanti, G.; Riva, R. Chem. Commun. 2000, 985-986.
17. Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869-872.
18. (a) Ibata, T.; Isogami, Y.; Tamura, H. Chem. Lett. 1988, 1551-1554.
19. (b) Suga, H.; Ibata, T. Chem. Lett. 1991, 1221-1224.
20. Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884-1888.