Synthesis and utilization of a novel glycine derived chiral precursor, based on a recyclable l-prolinol auxiliary, for the enantioselective preparation of α-amino acids and their n-methyl derivatives

Tetrahedron Letters

Volumn 37, Issue 18, 1996, Pages 3175-3178

  Pandey, Ganesh ^a   Reddy, P Yella ^a   Parthasarathi, Das ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029965308     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00488-1     Document Type: Article

References (22)

1. O'Donnel, M. J. (Ed.) Tetrahedron Symposia-in-print 1988, 44, 5253.
2. b) Williams, R. M. Organic Chemisrty Series Vol. 7 "Synthesis of Optically Active α-amino acids"; Baldwin, J. E.; Magnus, P. D. (Ed.) Pergamon Press; Oxford 1989.
3. c) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149.
4. d) Duthaler, R. O. Tetrahedron 1994, 50, 1539.
5. For recent synthetic approaches for the preparation of N-methyl-L-amino acids see a) Groeger, U.; Drauz, K.; Klenk, H. Angew. Chem. Int. Ed. (Engl.) 1992, 195.
6. b) Xue, C-B; DeGrado, W. F. Tetrahedron Lett., 1995, 36, 55 and references cited therein.
7. a) Kleinkauf, H.; von Dohren, H., Regulation of Secondary Metabolic Formation Kleinkauf, H.; Dohren von, H. Dornauer, H.; Nesemann, G. (Eds.) VCH, Weinheim 1986, 173-207 and references cited therein,
8. b) Mazur, R. H.; James, P. A.; Tyner, D. A.; Halllinan, E. A.; Sannen, J. H.; Schulze, R. J. Med. Chem. 1980, 23, 758. and references cited therein.
9. Oppolzer, W.; Moretti, R.; Zhou, C. Helv. Chem. Acta. 1994, 77, 2363 and references cited therein.
10. Pandey, G.; Kumarswamy, G.; Reddy, P. Y. Tetrahedron 1992, 48, 8295.
11. b) Pandey, G.; Reddy, P. Y.; Bhalerao, U. T. Tetrahedron Lett. 1991, 32, 5147.
12. Lewis, F. D. Acc. Chem. Res. 1986, 19, 401 and references cited therein.
13. f values and the major diastereomer could be isolated in pure form only for spectral purposes. We could not purify diastereomers individually in sufficient amounts for synthetic transformations and therefore 1 was used as such for further transformations.
14. Burnett, D. A.; Choi, J. K.; Hart, D. J.; Tsai, Y. M. J. Am. Chem. Soc. 1984, 106, 8201.
15. Wu, M. J.; Pridgen, L. N. J. Org. Chem. 1991, 56, 1340.
16. b) Alberola, A.; Andres, C; Pedrosa, R. Synlett 1990, 763.
17. Negligible racemisation during the hydrolysis of 6 was observed as the enantiomeric excess of corresponding esters (determined by analysing over chiral GC column) matched with the diastereomeric ratios of 6a and 6b.
18. Olofson, R. A.; Martz, T. J.; Senet, J. P.; Piteau, M.; Malfroot, T. J.Org. Chem 1984, 49, 2081.
19. Reetz, M. T.; Kesserler,; Schmidtberger, S.; Wenderroth, B.; Steinbach, R. Angew. Chem.Int. Ed. (Engl.) 1983, 989.
20. Still, W. C.; McDonald, J. H. Tetrahedron Lett, 1980, 21, 1031.
21. b) Still, W. C.; Schneider, J. A. Tetrahedon Lett. 1980, 21, 1035.
22. Guo, Z-X.; Schaeffer, M. J.; Taylor, J. K. J. Chem. Soc. Chem. Commun. 1993, 874.