Easy access to α-amino β-oxo esters from β-enamino esters

Tetrahedron Letters

Volumn 40, Issue 23, 1999, Pages 4413-4416

  Felice, Elena ^a   Fioravanti, Stefania ^a   Pellacani, Lucio ^a   Tardella, Paolo A ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Amination; Amino acids and derivatives

Indexed keywords

ALPHA AMINO ACID; ETHYL 2 [(ETHOXYCARBONYL)AMINO] 3 OXOBUTANOATE; HYDROXYAMINO ACID; N [(4 NITROBENZENESULPHONYL)OXY]CARBAMATE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; CHIRALITY; DIASTEREOISOMER; REACTION ANALYSIS;

EID: 0033523055     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00760-1     Document Type: Article

References (23)

1. Fioravanti, S.; Pellacani, L.; Tabanella, S.; Tardella, P. A. Tetrahedron 1998, 54, 14105-14112.
2. Fioravanti, S.; Pellacani, L.; Tardella, P. A. Gazz. Chim. Ital. 1997, 127, 41-44 and refs. therein.
3. Fioravanti, S.; Pellacani, L.; Stabile, S.; Tardella, P. A.; Ballini, R. Tetrahedron 1998, 54, 6169-6179.
4. The Chemistry of Enamines. Part I; Rappoport, Z., Ed. (The Chemistry of Functional Groups; Patai, S.; Rappoport, Z., Eds.); John Wiley & Sons: Chichester, 1994.
5. Fioravanti, S.; Pellacani, L.; Ricci, D.; Tardella, P. A. Tetrahedron: Asymmetry 1997, 8, 2261-2266.
6. Whitesell, J. K.; Minton, M. A.; Chen, K. M. J. Org. Chem. 1988, 53, 5383-5384; Dankwardt, J. W.; Dankwardt, S. M.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4983-4986 and refs. therein.
7. Whitesell, J. K.; Minton, M. A.; Chen, K. M. J. Org. Chem. 1988, 53, 5383-5384; Dankwardt, J. W.; Dankwardt, S. M.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4983-4986 and refs. therein.
8. Lwowski, W.; Maricich, T. J. J. Am. Chem. Soc. 1965, 87, 3630-3637.
9. Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39-42; Di Giovanni, M. C.; Misiti, D. Zappia, G.; Delle Monache G. Gazz. Chim. Ital. 1997, 127, 475-481; Choi, S. K.; Lee, J. S.; Kim, J. H.; Lee, W. K. J. Org. Chem. 1997, 62, 743-745.
10. Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39-42; Di Giovanni, M. C.; Misiti, D. Zappia, G.; Delle Monache G. Gazz. Chim. Ital. 1997, 127, 475-481; Choi, S. K.; Lee, J. S.; Kim, J. H.; Lee, W. K. J. Org. Chem. 1997, 62, 743-745.
11. Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39-42; Di Giovanni, M. C.; Misiti, D. Zappia, G.; Delle Monache G. Gazz. Chim. Ital. 1997, 127, 475-481; Choi, S. K.; Lee, J. S.; Kim, J. H.; Lee, W. K. J. Org. Chem. 1997, 62, 743-745.
12. Fioravanti, S.; Olivieri, L.; Pellacani, L.; Tardella, P. A. Tetrahedron Lett. 1998, 39, 6391-6392.
13. Fioravanti, S.; Olivieri, L.; Pellacani, L.; Tardella, P. A. J. Chem. Res., Synop. 1998, 338-339.
14. The substrate itself or alternatively traces of pyrrolidine either present or formed in the reaction medium could act as the base.
15. The filtered crude mixture of 3 was reduced into 5 and then purified by flash chromatography (hexane/ethyl acetate, 9:1).
16. +, 0.14), 130 (100), 102 (10), 86 (14), 58 (68), 56 (14), 41 (13).
17. +, 9), 313 (49), 268 (12), 267 (79), 193 (12), 184 (40), 163 (10), 135 (17), 111 (26), 109 (13), 81 (15), 79 (16), 75 (24), 71 (100), 68 (43), 55 (12), 45 (48), 41 (27), 29 (35).
18. Fuji, K. Chem. Rev. 1993, 93, 2037-2066.
19. Guingant, A.; Hammami, H. Tetrahedron: Asymmetry 1991, 2, 411-414.
20. +, 7), 128 (10), 127 (100), 114 (54), 101 (11), 82 (10), 55 (35).
21. Short, R. P.; Kennedy, R. M.; Masamune, S. J. Org. Chem. 1989, 54, 1755-1756.
22. +, 2), 226 8100), 114 (12), 82 (12), 71 (45), 45 (17).
23. +, 18), 211 (12), 185 (12), 184 (99), 156 (100), 140 (24), 139 (11), 138 (44), 112 (84), 110 (11), 84 (70), 82 (23), 67 (27), 55 (21), 54 (32), 41 (19).