A new diastereoselective synthesis of anti-α-alkyl α-hydroxy β-amino acids

European Journal of Organic Chemistry

Volumn , Issue 1, 1999, Pages 155-161

  Cardillo, Giuliana ^a   Tolomelli, Alessandra ^a   Tomasini, Claudia ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Alkylation; Anti Alkyl hydroxy amino acids; Lithium dianion; Oxazolines; Penicillin G acylase

Indexed keywords

AMIDASE; AMIDE; BETA AMINO ACID; BUTYRIC ACID; OXAZOLINE DERIVATIVE; PROPIONIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; ENANTIOMER; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032784177     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199901)1999:1<155::aid-ejoc155>3.0.co;2-a     Document Type: Article

References (28)

1. [1a] Enantioselective Synthesis of β-Amino Acids (Ed.: E. Juaristi), VCH Publishers, New York, 1996 and references therein.
2. [1b] D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
3. [1c] E. Juaristi, D. Quintana, J. Escalante, Aldrichim. Acta 1994, 27, 3-11.
4. [1d] G. Cardillo, C. Tomasini, Chem. Soc. Rev. 1996, 25, 117-128.
5. See for example: K. C. Nicolaou, W-M. Dai, R. K. Guy, Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44, and references therein.
6. M. Hepperle, G. I. Georg, Drugs of the Future 1994, 19, 573-584.
7. J. Kant, W. S. Schwartz, C. Fairchild, Q. Gao, S. Huang, B. H. Long, J. F. Kadow, D. R. Langley, V. Farina, D. Vyas, Tetrahedron Lett. 1996, 37, 6495-6498, and references therein.
8. [5a] G. Cardillo, L. Gentilucci, A. Tolomelli, C. Tomasini. J. Org. Chem. 1998, 63, 2351-2353.
9. [5b] G. Cardillo, A: Tolomelli, C. Tomasini, Tetrahedron 1995, 51, 11831-11840.
10. See for example: [6a] R. Grandel, U. Kazmaier, Eur. J. Org. Chem. 1998, 409-417.
11. [6b] Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, A. A. Chesnokov, O. V. Larionov, V. S. Parmar, R. Kumar, H. B. Kagan, Tetrahedron: Asymmetry 1998, 9, 851-857.
12. [6c] T. Wirth, Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
13. [6d] R. Chinchilla, L. Falvello, N. Galindo, C. Najera, Angew. Chem. Int. Ed. Engl. 1997, 36, 995-997, and references therein.
14. [7a] I. Ojima, T. Wang, F. Delaloge, Tetrahedron Lett. 1998, 39, 3663-3666.
15. [7b] J.-N. Denis, A. Fkyerat, Y. Gimbert, C. Coutterez, P. Mantellier, S. Jost, A. E. Greene, J. Chem. Soc., Perkin Trans. 1 1995, 1811-1815. -For the synthesis of α-methylisoserine see:
16. [7c] C. Cativiela, M. D. Diaz-de-Villegas, J. A. Galvez, Tetrahedron 1996, 52, 687-694.
17. [7d] R. Pires, K. Burger, Synthesis 1996, 1277-1279.
18. W. M. Rodionow, E. A. Postovskaja, J. Am. Cliem. Soc. 1929, 51, 841-852.
19. E. Baldaro, C. Fuganti, S. Servi, A. Tagliani, M. Terreni in Microbial Reagents in Organic Synthesis (Ed.: S. Servi), Kluwer Academic Publishers, Netherlands, 1992, p. 175-188.
20. [10a] D. Rossi, G. Lucente, A. Romeo, Experientia 1977, 33, 1557-1559.
21. [10b] V. A. Soloshonok, V. K. Svedas, V. P. Kukhar, A. G. Kirilenko, A. V. Rybakova, V. A. Solodenko, N. A. Fokina, O. V. Kogut, I. Y. Galaev, E. V. Kozlova, I. P. Shishkina, S. V. Galushko, Synlett 1993, 339-341.
22. [10c] V. A. Soloshonok, N. A. Fokina, A. V. Rybakova, I. P. Shishkina, S. V. Galushko, A. E. Sorochinsky, V. P. Kukhar, M. V. Savchenko, K. V. Svedas, Tetrahedron: Asymmetry 1995, 7, 1601-1610.
23. [10d] A. L. Margolin, Tetrahedron Lett. 1993, 34, 1239-1242.
24. [11a] D. Seebach, J. D. Aebi, M. Gander-Coquoz, R. Naef, Helv. Chim. Acta 1987, 70, 1194-1216.
25. [11b] D. Seebach, J. D. Aebi, Tetrahedron Lett. 1983, 24, 3311-3314.
26. See for example: G. Cainelli, D. Giacomini, M. Waltz, Angew. Chem. Int. Ed. Engl. 1995, 34, 2150-2152.
27. A racemic synthesis of this compound has been performed: H. Estermann, D. Seebach, Helv. Chim. Acta 1988, 71, 1824-1840.
28. D.-M. Gou, Y.-C. Liu, C.-S. Chen, J. Org. Chem. 1993, 58, 1287-1289.