Tricarbonyl(η6arene)chroimum(0) complexes as chiral auxiliaries: Asymmetric synthesis of β-aminoesters and β-lactams by Reformatsky condensation

Tetrahedron

Volumn 52, Issue 13, 1996, Pages 4849-4856

  Baldoli, Clara ^a   Del Buttero, Paola ^a   Licandro, Emanuela ^a   Papagni, Antonio ^a   Pilati, Tullio ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BETA LACTAM DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029972809     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00156-1     Document Type: Article

References (30)

1. Oilman, H.; Speeter, M. J. Am. Chem. Soc., 1943, 65, 2255-2256.
2. Dardoize, F.; Moreau, J.L.; Gaudeman, M. Bull. Chem. Soc. Fr., 1973, 5, 1668-1672.
3. Luche, J.L.; Kagan, H.B. Bull. Chem. Soc. Fr., 1971, 6, 2260-2261.
4. Baldoli, C.; Del Buttero, P. J. Chem. Soc. Chem. Commun., 1991, 982-984.
5. Baldoli, C.; Del Buttero, P.; Licandro, E.; Maiorana, S.; Papagni, A. Synlett, 1994, 183-185.
6. Baldoli, C.; Del Buttero, P.; Licandro, E.; Maiorana, S.; Papagni, A. Tetrahedron: Asymmetry, 1994, 5, 809-812.
7. Han, B. H.; Boudjouk, P. J. Org. Chem., 1982, 47, 5030-5032; Bose, A.K.; Gupta, K.; Manhas, M.S. J. Chem. Soc. Chem. Commun., 1984, 86-87.
8. Han, B. H.; Boudjouk, P. J. Org. Chem., 1982, 47, 5030-5032; Bose, A.K.; Gupta, K.; Manhas, M.S. J. Chem. Soc. Chem. Commun., 1984, 86-87.
9. When the sonication reaction was performed at 40-45°C instead of 20-25°C, no appreciable change in the ratio of β-aminoesther 8 and β-lactam 11 (53:42) was obtained, but only a decrease in the yield and diastereoselection (d.e.= 65%).
10. Ojima, I.; Inaba, S.; Yoshida, K. Tetrahedron Lett., 1977, 41, 3643-3646.
11. Barrow, K.D.; Spotswood, T.M. Tetrahedron Lett., 1965, 37, 3325-3335; Luche, J.L.; Kagan, H.B. Tetrahedron, 1967, 24, 1275-1281.
12. Barrow, K.D.; Spotswood, T.M. Tetrahedron Lett., 1965, 37, 3325-3335; Luche, J.L.; Kagan, H.B. Tetrahedron, 1967, 24, 1275-1281.
13. 4 respectively. S2pull sequence and ADDSUB routine for FID difference were used. An about 14% NOE was obtained only in the case of the trans isomer.
14. Künding, E.P.; Xu, L.H.; Schnell, B. Synlett, 1995, 413-414.
15. Rehling, H.; Jensen, H. Tetrahedron Lett., 1972, 27, 2793-2796; Galle, D.; Tolksdorf, M.; Braun, M. Tetrahedron Lett., 1995, 36, 4217-4220.
16. Rehling, H.; Jensen, H. Tetrahedron Lett., 1972, 27, 2793-2796; Galle, D.; Tolksdorf, M.; Braun, M. Tetrahedron Lett., 1995, 36, 4217-4220.
17. Pietsch, H. Tetrahedron Lett., 1972, 27, 2789-2792.
18. Pirkle, W.H.; Tsipouras, A.; Hyun, M.H.; Hart, D.J.; Lee, C.S. J. Chromatogr., 1986, 255, 377-384.
19. Davies, S.G.; Walters, I.A.S. J. Chem. Soc. Perkin Trans.1, 1994, 1129-1139; Davies, S.G.; Ichihara, O.; Walters, I.A.S. ibid., 1994, 1141-1147.
20. Davies, S.G.; Walters, I.A.S. J. Chem. Soc. Perkin Trans.1, 1994, 1129-1139; Davies, S.G.; Ichihara, O.; Walters, I.A.S. ibid., 1994, 1141-1147.
21. Abrahams, I.; Motevalli, M.; Robinson, J.A.; Wyatt, P.B. Tetrahedron, 1994, 50, 12755-12772.
22. The C-4 stereodescriptor change from 15 (3-unsubstituted) or 16 (3-methyl substituted) to 17.
23. Panajotova, B.D.; Berova, N.D.; Simova, E.M. Compt. Rend. Acad. Bulg. Sci., 1985, 38, 591-594; Shimizu, M.; Teramoto, Y.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 729-732.
24. Panajotova, B.D.; Berova, N.D.; Simova, E.M. Compt. Rend. Acad. Bulg. Sci., 1985, 38, 591-594; Shimizu, M.; Teramoto, Y.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 729-732.
25. 22 whose final value was 0.01(3).
26. Altomare, A.; Cascarano, G.; Giacovazzo, G.; Guagliardi, A.; Burla, M.C.; Polidori, G.; Camalli, M. Jour. Appl. Cryst., 1994, 27, 435-436.
27. Sheldrick, G.M. 1993, Program for the Refinement of Crystal Structure, UNIV. Göttingen, Germany.
28. Flack, H.D. Acta Cryst., 1983, A39, 876-881.
29. Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F., Tetrahedron, 1995, 51, 8941-8952.
30. Shimizu, M.; Teramoto, Y.; Fujisawa, T. "Corrigendum" note Tetrahedron Lett., 1995, 36, 4324.