Addition of organolithium reagents to Ahc methyl ester. An approach to new α-amino ketones

Tetrahedron

Volumn 58, Issue 51, 2002, Pages 10167-10171

  Avenoza, Alberto ^a   Busto, Jesús H ^a   Peregrina, Jesús Manuel ^a  

^a UNIVERSITY OF LA RIOJA   (Spain)

Author keywords

Acylation; Amino acids and derivatives; Amino ketones; Bicyclic heterocyclic compounds; Lithium and compounds

Indexed keywords

(N BENZOYL 7 AZABICYCLO[2.2.1]HEPT 1 YL)PHENYLKETONE; (N BENZOYL 7 AZABICYCLO[2.2.1]HEPT 1 YL)PYRIDIN 3 YLKETONE; 1 (N BENZOYL 7 AZABICYCLO[2.2.1]HEPT 1 YL)METHYLKETONE; 1 (N BENZOYL 7 AZABICYCLO[2.2.1]HEPT 1 YL)SEC BUTYLKETONE; 1 (N BENZOYL 7 AZABICYCLO[2.2.1]HEPT 1 YL)TERT BUTYLKETONE; ACETAL DERIVATIVE; AMINOKETONE; AMMONIUM CHLORIDE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; METHYL N BENZOYL 7 AZABICYCLO[2.2.1]HEPTANE 1 CARBOXYLATE; ORGANOLITHIUM COMPOUND; REAGENT; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; METHODOLOGY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0037121778     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01363-7     Document Type: Article

References (25)

1. Sardina F.J., Rapoport H. Chem. Rev. 96:1996;1825-1872.
2. Reetz M.T. Angew. Chem., Int. Ed. Engl. 30:1991;1531-1546.
3. Sawamura M., Nakayama Y., Kato T., Ito Y. J. Org. Chem. 60:1995;1727-1732.
4. Pace R.P., Kabalka G.W. J. Org. Chem. 60:1995;4838-4844.
5. O'Neil B.T. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 1:1991;397-458 Pergamon, Oxford.
6. Nahm S., Weinreb S.M. Tetrahedron Lett. 22:1981;3815-3818.
7. Sibi M.P. Org. Prep. Proced. Int. 25:1993;15-40.
8. Buckley T.F. III, Rapoport H. J. Am. Chem. Soc. 103:1981;6157-6163.
9. Rommele R.C., Rapoport H. J. Org. Chem. 54:1989;1866-1875.
10. Barluenga J., Baragaña B., Concellón J.M. J. Org. Chem. 60:1995;6696-6699.
11. Fernández-Megía E., Iglesias-Pintos J.M., Sardina F.J. J. Org. Chem. 62:1997;4770-4779.
12. Paleo M.R., Sardina F.J. Tetrahedron Lett. 19:1996;3403-3406.
13. Paleo M.R., Calaza M.I., Sardina F.J. J. Org. Chem. 62:1997;6862-6869.
14. Hirashima S., Aoyagi S., Kibayashi C. J. Am. Chem. Soc. 121:1999;9873-9874.
15. Barrett A.G.M., Damiani F. J. Org. Chem. 64:1999;1410-1411.
16. Okamoto S., Iwakubo M., Kobayashi K., Sato F. J. Am. Chem. Soc. 119:1997;6984-6990.
17. Goldstein S.W., Overman L.E., Rabinowitz M.H. J. Org. Chem. 57:1992;1179-1190.
18. Avenoza A., Cativiela C., Corzana F., Peregrina J.M., Zurbano M.M. J. Org. Chem. 64:1999;8220-8225.
19. Avenoza A., Busto J.H., Cativiela C., París M., Peregrina J.M. J. Heterocycl. Chem. 34:1997;1099-1110.
20. Avenoza A., Cativiela C., Díaz-de-Villegas M.D., Peregrina J.M. Tetrahedron. 49:1993;10987-10996.
21. Avenoza A., Busto J.H., Cativiela C., Peregrina J.M., Fernández-Recio M.A., Rodríguez F. Tetrahedron. 57:2001;545-548.
22. Avenoza A., Busto J.H., Cativiela C., Peregrina J.M. Tetrahedron. 58:2002;1193-1197.
23. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, Jr., R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.11; Gaussian, Inc.: Pittsburgh PA, 2001.
24. Barluenga J., Pedregal B., Concellón J.M. Tetrahedron Lett. 34:1993;4563-4564.
25. Creary X. J. Org. Chem. 52:1987;5026-5030.