New expedient route to both enantiomers of nonproteinogenic α-amino acid derivatives from the unsaturated 2-aza-bicyclo moiety

Journal of Organic Chemistry

Volumn 64, Issue 7, 1999, Pages 2276-2280

  Alonso, Diego A ^a   Bertilsson, Sophie K ^a   Johnsson, Sandra Y ^a   Nordin, Sofia J M ^a   Södergren, Mikael J ^a   Andersson, Pher G ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZA BICYCLO HEPT 5 ENE; ALPHA AMINO ACID; AMINO ACID DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CATALYSIS; CHIRALITY; HYDROGENATION;

EID: 0033515506     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981838w     Document Type: Article

References (41)

1. (a) Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of chiral molecules using amino acids; John Wiley & Sons: New York, 1987.
2. (b) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989.
3. (c) Duthaler, R. H. Tetrahedron 1994, 50, 1539.
4. (d) Barrett, G. C., Ed. Chemistry and Biochemistry of the Amino Acids; Chapman and Hall: London, 1985.
5. Hanessian, S.; Franco, J.; Larouche, B. Pure Appl. Chem. 1990, 62, 1887.
6. (a) Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
7. (b) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
8. (c) Xavier, L. C.; Mohan, J. J.; Mathre, D. J.; Tompson, A. S.; Carroll, J. D.; Corley, E. G.; Desmond, R. Organic Syntheses; Wiley: New York, 1997; Vol. 74, p 51.
9. (d) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897.
10. (a) Evans, D. A.; Nelson, S. G. J. Am. Chem. Soc. 1997, 119, 6452.
11. (b) Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207.
12. (c) Lee, J.; Choi, W.-B.; Lynch, J. E.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 3679.
13. (d) Sabelle, S.; Lucet, D.; Gall, T. L.; Mioskowski, C. Tetrahedron Lett. 1998, 39, 2111.
14. (a) Södergren, M. J.; Andersson, P. G. Tetrahedron Lett. 1996, 37, 7577.
15. (b) Alonso, D. A.; Guijarro, D.; Pinho, P.; Temme, O.; Andersson, P. G. J. Org. Chem. 1998, 63, 2749.
16. (c) Pinho, P.; Guijarro, D.; Andersson, P. G. Tetrahedron 1998, 54, 7897.
17. (d) Södergren, M. J.; Andersson, P. G. J. Am. Chem. Soc. 1998, 120, 10760.
18. (e) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530.
19. (f) Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391.
20. (a) Nakano, H.; Iwasa, K.; Hongo, H. Heterocycles 1997, 44, 435.
21. (b) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233.
22. (a) Stella, L.; Abraham, H.; Feneu-Dupont, J.; Tinant, B.; Declercq, J. P. Tetrahedron Lett. 1990, 31, 2603.
23. (b) Abraham, H.; Stella, L. Tetrahedron 1992, 48, 9707.
24. (a) Rylander, P. N. Hydrogenation Methods; Academic Press: London, 1985;
25. (b) p 167;
26. (c) p 10.
27. (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
28. (b) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825.
29. (c) Hoffman, R. V.; Tao, J. Tetrahedron 1997, 53, 7119.
30. Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518.
31. Waldmann, H.; Braun, M. Liebigs Ann. Chem. 1991, 1045.
32. Haaseth, R. C.; Horan, P. J.; Bilsky, E. J.; Davis, P.; Zalewska, T.; Slaninova, J.; Yamamura, H. I.; Weber, S. J.; Davis, T. P.; Porreca, F.; Hruby, V. J. J. Med. Chem. 1994, 37, 1572.
33. (a) Williams, R. M.; Sinclair, P. J,; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547.
34. (b) Hill, J. T.; Dunn, F. W. J. Org. Chem. 1965, 30, 1321.
35. (c) Eisler, K.; Rudinger, J.; Sôrm, F. Collect. Czech. Chem. Commun. 1966, 31, 4563.
36. Klyne, W.; Scopes, P. M.; Thomas, R. N.; Dahn, H. Helv. Chim. Acta 1971, 54, 2420.
37. Mi'covi'c, V. M.; Mihailovi'c, M. L. J. Org. Chem. 1953, 18, 1190.
38. Meyers, A. I.; Knaus, G.; Kamata, K.; Ford, M. E. J. Am. Chem. Soc. 1976, 98, 567.
39. Dox, A. W. Organic Synthesis; Wiley: New York, 1941, Collect. Vol. I, p 5.
40. (a) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 773, 726.
41. (b) After completion of this work, a new improved method for synthesis of bisoxazoline ligands was published: Evans, D. A.; Peterson, G. S.; Johnson, J. S.; Barnes, D. M.; Campos, K. R.; Woerpel, K. A. J. Org. Chem. 1998, 63, 4541.