Synthesis of new β-amino acids via 5-oxazolidinones and the arndt-eistert procedure

Australian Journal of Chemistry

Volumn 58, Issue 11, 2005, Pages 778-784

  Hughes, Andrew B ^a   Sleebs, Brad E ^b  

^a LA TROBE UNIVERSITY   (Australia)

^b WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; DRUG PRODUCTS; LEAD COMPOUNDS; PROTEINS; REDUCTION; SYNTHESIS (CHEMICAL);

5-OXAZOLIDINONE; AMINO ACID DERIVATIVES; LEAD PEPTIDE THERAPEUTICS;

AMINO ACIDS;

EID: 29144532678     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH05199     Document Type: Article

References (18)

1. (a) L. Aurelio, R. T. C. Brownlee, A. B. Hughes, B. E. Sleebs, Aust. J. Chem. 2000, 53, 425. doi:10.1071/CH99082
2. (b) L. Aurelio, J. S. Box, R. T. C. Brownlee, A. B. Hughes, M. M. Sleebs, J. Org. Chem. 2003, 68, 2652. doi:10.1021/JO026722L
3. (a) K. N. White, J. P. Konopelski, Org. Lett. 2005, 7, 4111. doi:10.1021/OL051441W
4. (b) S. Zhang, T. Govender, T. Norstroem, P. Arvidsson, J. Org. Chem. 2005, 70, 6918. doi:10.1021/JO050916U
5. (c)E. Biron, K. Yamada, H. Oku, R. Katakai, J. Org. Chem. 2005, 70, 5183. doi:10.1021/JO050477Z
6. Enantioselective Synthesis of β-Amino Acids (Ed. E. Juaristi) 1997 (Wiley-VCH: New York).
7. A. Hassner, C. Stumer, Organic Synthesis Based on Name Reactions and Unnamed Reactions 1994 (Pergamon: Oxford).
8. K. Plucinska, B. Liberek, Tetrahedron 1987, 43, 3509. doi:10.1016/S0040-4020(01)81643-4
9. T. Kimmerlin, D. Seebach, Helv. Chim. Acta 2003, 86, 2098. doi:10.1002/HLCA.200390166
10. B. Penke, J. Czombos, L. Baláspiri, J. Petres, K. Kovács, Helv. Chim. Acta 1970, 53, 1057. doi:10.1002/HLCA.19700530520
11. D.S. Tarbell, J. A. Price, J. Org. Chem. 1957, 22, 245. doi:10.1021/JO01354A005
12. (a) K.-Y. Zee-Cheng, R. K. Robins, C. C. Cheng, J. Org. Chem. 1961, 26, 1877. doi:10.1021/JO01065A046
13. (b) D. Seebach, P. E. Ciceri, M. Overhand, B. Jaun, D. Rigo, Helv. Chim. Acta 1996, 79, 2043. doi:10.1002/HLCA.19960790802
14. E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds 1994, Ch. 11, p. 682 (Wiley: New York).
15. W. L. F. Armarego, D. D. Perrin, Purification of Laboratory Chemicals, 3rd edn 1988 (Pergamon Press: Oxford).
16. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923. doi:10.1021/JO00408A041
17. Diazomethane is very toxic and potentially explosive. For procedures on its preparation and safe handling see: (a) T. J. de Boer, H. J. Baker, Org. Synth. Collect. Vol. 4 1963, p. 250 (Wiley: New York, NY).
18. (b) M. Hudlicky, J. Org. Chem. 1980, 45, 5377. doi:10.1021/JO01314A036