An efficient synthesis of γ-amino β-ketoester by cross-Claisen condensation with α-amino acid derivatives

Tetrahedron Letters

Volumn 44, Issue 15, 2003, Pages 3163-3166

  Honda, Yutaka ^a   Katayama, Satoshi ^a   Kojima, Mitsuhiko ^a   Suzuki, Takayuki ^a   Izawa, Kunisuke ^a  

^a AJINOMOTO CO INC   (Japan)

Author keywords

Amino acid; Claisen condensation; Cross ester condensation; Lithium enolate; amino ketoester

Indexed keywords

ACETIC ACID DERIVATIVE; AMINO ACID DERIVATIVE; AMINO ACID ESTER; ESTER DERIVATIVE; GAMMA AMINO BETA KETOESTER; LITHIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; POLYMERIZATION; SYNTHESIS;

EID: 0037424783     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00464-7     Document Type: Article

References (43)

1. Ohta S., Shimabayashi A., Hayakawa S., Sumino M., Okamoto M. Synthesis. 1985;45-48.
2. Hauser C.R., Hudson B.E. Org. React. 1:1942;266-302.
3. Turner J.A., Jacks W.S. J. Org. Chem. 54:1989;4229-4231.
4. Trotter N.S., Takahashi S., Nakata T. Org. Lett. 1:1999;957-959.
5. Spino C., Mayes N., Desfosses H. Tetrahedron Lett. 37:1996;6503-6506.
6. Nakata T., Komatsu T., Nagasawa K. Chem. Pharm. Bull. 42:1994;2403-2405.
7. Shao L., Seki T., Kawano H., Saburi M. Tetrahedron Lett. 32:1991;7699-7702.
8. Deschenaux P.F., Kallimopoulos T., Stoeckli-Evans H., Jacot-Guillarmod A. Helv. Chim. Acta. 72:1989;731-737.
9. Shao L., Kawano H., Saburi M., Uchida Y. Tetrahedron. 49:1993;1997-2010.
10. Patel D.V., Schmidt R.J., Gordon E.M. J. Org. Chem. 57:1992;7143-7151.
11. Cardani S., Scolastico C., Villa R. Tetrahedron. 46:1990;7283-7288.
12. Jendralla H., Baader E., Bartmann W., Bech G., Bergmann A., Granzer E., v. Kerekjarto B., Kesseler K., Krause R., Schubert W., Wess G. J. Med. Chem. 33:1990;61-70.
13. Kitazume T., Ohnogi T., Lin J.T., Yamazaki T., Ito K. J. Fluorine Chem. 42:1989;17-29.
14. Winkler J.D., Hershberger P.M. J. Am. Chem. Soc. 111:1989;4852-4856.
15. Steulmann R., Klostermeyer H. Liebigs Ann. Chem. 1975;2245-2250.
16. Parkes K.E.B., Bushnell D.J., Crackett P.H., Dunsdon S.J., Freeman A.C., Gunn M.P., Hopkins A., Lambert R.W., Martin J.A., Merrett J.H., Redshaw S., Spurden W.C., Thomas G.J. J. Org. Chem. 59:1994;3656-3664.
17. Mansour T.S., Evans C.A. Synth. Commun. 20:1990;773-780
18. Palmer, J. T.; Prototek, Inc.; Eur. Pat. Appl., EP442754, 1991.
19. Kim H.-O., Oisen R.K., Choi O.-S. J. Org. Chem. 52:1987;4531-4536.
20. Ramanjulu J.M., Ding X., Joullie M.M., Li W.R. J. Org. Chem. 62:1997;4961-4969.
21. Dufour M.-N., Jouin P., Poncet J., Pantaloni A., Castro B. J. Chem. Soc., Perkin Trans. 1. 1986;1895-1899.
22. Paris M., Fehrents J.A., Heitz A., Loffet A., Martinez J. Tetrahedron Lett. 37:1996;8489-8492.
23. Palomo C., Cossio F.P., Rubiales G., Aparicio D. Tetrahedron Lett. 32:1991;3115-3118.
24. Hoffman R.V., Tao J. J. Org. Chem. 62:1997;2292-2297.
25. Hoffman R.V., Tao J. Tetrahedron. 53:1997;7119-7126.
26. Tao J., Hoffman R.V. J. Org. Chem. 62:1997;6240-6244.
27. Hoffman R.V., Kim H.-O. Tetrahedron Lett. 33:1992;3579-3582.
28. Jouin P., Poncet J., Dufour M.-N., Maugras I., Pantaloni A., Castro B. Tetrahedron Lett. 29:1988;2661-2664.
29. Ino A., Hasegawa Y., Murabayashi A. Tetrahedron Lett. 39:1998;3509-3512.
30. Harris B.D., Bhat K.L., Joullie M.M. Tetrahedron Lett. 28:1987;2837-2840.
31. Wagner B., Beugelmans R., Zhu J. Tetrahedron Lett. 37:1996;6557-6560.
32. Li W.-R., Ewing W.R., Harris B.D., Joullie M.M. J. Am. Chem. Soc. 112:1990;7659-7672.
33. Hoffman R.V., Weiner W.S., Maslouh N. J. Org. Chem. 66:2001;5790-5995.
34. Honda Y., Katayama S., Kojima M., Suzuki T., Izawa K. Org. Lett. 4:2002;447-449
35. Honda, Y.; Katayama, S.; Izawa, K.; Ajinomoto Co., Inc.; Eur. Pat. Appl., EP1097919, May 9, 2001;
36. Honda, Y.; Katayama, S.; Izawa, K.; Nakazawa, M.; Suzuki, T.; Kanno, N.; Ajinomoto Co., Inc.; U.S. Patent 5 902 887, May 11, 1999;
37. Honda, Y.; Katayama, S.; Izawa, K.; Nakazawa, M.; Suzuki, T.; Kanno, N.; Ajinomoto Co., Inc.; U.S. Patent 5 767 316, Jun 16, 1998.
38. Reetz M.R., Drewes M.W., Schmitz A. Angew. Chem., Int. Ed. Engl. 26:1987;1141-1143.
39. +).
40. Dinh T.Q., Du X., Armstrong R.W. J. Org. Chem. 61:1996;6606-6616.
41. Sewald N., Hiller K.D., Koerner M., Findeisen M.J. J. Org. Chem. 63:1998;7263-7274.
42. Asao N., Uyehara T., Yamamoto Y. Tetrahedron. 46:1990;4563-4572.
43. Davies S.G., Walters I.A.S. J. Chem. Soc., Perkin Trans. 1. 1994;1129-1139.