Synthesis of highly enantio-enriched α-amino acids by carboxylation of N-(α-lithioalkyl)oxazolidinones

European Journal of Organic Chemistry

Volumn , Issue 7, 2000, Pages 1297-1305

  Jeanjean, Fabien ^a   Fournet, Guy ^a   Bars, Didier Le ^b   Goré, Jacques ^a  

^a UNIVERSITÉ LYON 1   (France)

^b CERMEP IMAGERIE DU VIVANT   (France)

Author keywords

Asymmetric synthesis; Carboxylation; Isotopic labelling; N ( Lithioalkyl)oxazolidin 2 ones; Amino acids

Indexed keywords

ALANINE; ALPHA AMINO ACID; HOMOCYSTEINE; LEUCINE; METHIONINE; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CARBOXYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; ISOTOPE LABELING; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0034095339     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200004)2000:7<1297::AID-EJOC1297>3.0.CO;2-L     Document Type: Article

References (39)

1. Reviews: [1a] R. M. Williams, R. M., Synthesis of Optically Active α-Amino Acids, Organic Chemistry Series, vol 7 (Ed.: J. E. Baldwin, P. D. Magnus), Pergamon Press, Oxford 1989.
2. [1b] R. O. Duthaler, Tetrahedron. 1994, 50, 1539-1650.
3. [1c] D. Seebach, A. R. Sting, H. Hoffmann, Angew. Chem. Int. Ed. Engl. 1996, 35, 2709-2748. - For recent references, see also:
4. [1d] L. Meyer, J. M. Poirier, P. Duhamel, L. Duhamel, J. Org. Chem. 1998, 63, 8094-8095 and references cited therein.
5. For a review on the Strecker synthesis, see ref. [1a] pp 208-229.
6. [3a] M. S. Patel, M. Worsley, Can. J. Chem. 1970, 48, 1881-1884. For more recent examples on asymmetric Strecker synthesis see:
7. [3b] G. Dyker, Angew. Chem. Int. Ed. Engl. 1997, 36, 1700-1702.
8. [3c] D. Ma, H. Tian, G. Zou, J. Org. Chem. 1999, 64, 120-125 and references cited therein.
9. P. Beak, S. T. Kerrick, J. Am. Chem. Soc. 1991, 113, 9708-9710.
10. [5a] M. Schlosser, D. Limat, J. Am. Chem. Soc. 1995, 117, 12342-12343.
11. [5b] N. Voyer, J. Roby, Tetrahedron Lett. 1995, 36, 6627-6630.
12. L. Duhamel, P. Duhamel, S. Fouqay, J. J. Eddine, O. Peschard, J. C. Plaquevent, A. Ravard, R. Solliard, J. Y. Valnot, H. Vicens, Tetrahedron 1988, 44, 5495-5506.
13. F. Jeanjean, N. Pérol, J. Goré, G. Fournet, Tetrahedron Lett. 1997, 38, 7547-7550.
14. D. Comar, PET for Drug Development and Evaluation, Kluwer Academic Publishers, Dodrecht, 1995.
15. P. Bobillier, E. Grange, A. Gharib, M. Leclerc, N. Sarda, P. Lepetit, in PET Studies on Amino Acid Metabolism and Protein Synthesis, Kluwer Academic Publishers, Dodrecht, 1993, 41-52.
16. J. M. Bolste, W. Vaalburg, Ph. H. Elsinga, H. Wynberg, M. G. Woldring, Appl. Radiat, Isot. 1986, 37, 1069-1070.
17. For α-nitrogen lithiation with (R)-Li-Sparteine see: [11a] Y. S. Park, M. L. Boys, P. Beak, J. Am. Chem. Soc. 1996, 118, 3757-3758.
18. [11b] P. Beak, A. Basu, D. J. Gallagher, Y. S. Park, S. Thayumanavan, Acc. Chem. Res. 1996, 29, 552-560.
19. [11c] Y. S. Park, P. Beak, J. Org. Chem. 1997, 62, 1574-1575.
20. [11d] D. Hoppe, T. Hense, Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316 and references cited therein.
21. [12a] W. H. Pearson, A. C. Lindbeck, J. Am. Chem. Soc. 1991, 113, 8546-8548.
22. [12b] W. H. Pearson, A. C. Lindbeck, J. W. Kampf, J. Am. Chem. Soc. 1993, 115, 2622-2636.
23. For reviews on oxazolidinones as chiral auxilliar es, see: [13a] D. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 835-875.
24. [13b] D. Ager, I. Prakash, D. R. Schaad, Aldrichinica Acta 1997, 30, 3-11.
25. [14a] S. Ram, L. D. Spicer, Synthetic Commun. 1987, 17, 415-418.
26. [14b] W. H. Pearson, A. C. Lindbeck, J. Org. Chem. 1989, 54, 5651-5654.
27. [15a] D. A. Evans, E. B. Sjogren, Tetrahedron Lett. 1985, 26, 3783-3786.
28. [15b] I. Ojima, H. J. C. Chen, X. Qiu, Tetrahedron 1988, 44, 5307-5318.
29. [15c] See also: S. Sabelle, D. Lucet, T. Le Gall, C Mioskowski, Tetrahedron Lett. 1998, 39, 2111-2114.
30. [16a] F. Jeanjean, PhD thesis, Univ. Lyon, 1999.
31. [16b] F. JeanJean, G. Fournet, D. Lebars, N. Roidot, L. Vichot, J. Goré, D. Comar. J. Lab. Comp. Radiopharm. 1997, 12, 722-724.
32. D. Le Bars, F. Jeanjean, G. Fournet, to be published.
33. J. R. Catch, A. H. Cook, A. R. Graham, J. Chem. Soc. 1947, 1609-1613.
34. [19a] J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 73, 512-519.
35. [19b] W. Breuer, I. Ugi, J. Chem. Research (S) 1982, 271; J. Chem. Research (S), 2901-2945.
36. [19b] W. Breuer, I. Ugi, J. Chem. Research (S) 1982, 271; J. Chem. Research (S), 2901-2945.
37. [19c] W. E. Hull, K. Seeholzer, M. Baumeister, I. Ugi, Tetrahedron 1986, 42, 547-552.
38. [20a] T Akiba, O Tamura, S. Terashima, Org. Synth. 1997, 75, 45-52.
39. [20b] H. S. Knölker, T. Braxmeir, Tetrahedron Lett. 1998, 39, 9407-9410.