Diastereoselective synthesis of β2-amino acids

European Journal of Organic Chemistry

Volumn , Issue 1, 2000, Pages 83-90

  Ponsinet, Rachel ^a   Chassaing, Gérard ^a   Vaissermann, Jacqueline ^a   Lavielle, Solange ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Amino acids; Diastereoselective alkylation; Oppolzer's sultam; Sultam imine enolate

Indexed keywords

BETA AMINO ACID; CARBOXYLIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033987613     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200001)2000:1<83::aid-ejoc83>3.0.co;2-2     Document Type: Article

References (35)

1. [1a] P. Dado, S. H. Gellman, J. Am. Chem. Soc. 1994, 116, 1054-1062.
2. [1b] D. Seebach, M. Overhand, F. N. Kühnle, B. Martinoni, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta. 1996, 79, 913-941.
3. [1c] D. Seebach, P. E. Ciceri, M. Overhand, B. Jaun, D. Rigo, L. Oberer, U. Hommel, R. Amstutz, H. Widmer, Helv. Chim. Acta. 1996, 79, 2043-2066.
4. [1d] D. H. Appella, L. A. Christianson, I. Karle, D. R. Powell, S. H. Gellman, J. Am. Chem. Soc. 1996, 118, 13071-13072.
5. [1e] T. Hintermann, D. Seebach, Synlett 1997, 437-438.
6. [1f] Review: D. Seebach, J. L. Matthews, Chem. Commun. 1997, 2015-2022.
7. [1g] X Daura, W. F. van Gunsteren, D. Rigo, B. Jaun, D. Seebach, Chem. Eur. J. 1997, 3, 1410-1417.
8. [1h] T. Hintermann, D. Seebach, Chimia 1997, 50, 244-247.
9. [1i] J. L. Matthews, M. Overhand, F. N. Kühnle, P. E. Ciceri, D. Seebach, Liebigs Ann.lRecueil 1997, 1371-1379.
10. [1j] D. H. Appella, L. A. Christianson, D. A. Klein, D. R. Powell, X. Huang, J. A. Barchi, Jr., S. H. Gellman, Nature 1997, 387, 381-384.
11. [1k] D. Seebach, S. Abele, K. Gademann, G. Guichard, T. Hintermann, B. Jaun, J. L. Matthews, J. V. Schreiber, L. Oberer, U. Hommel, H. Xidmer, Helv. Chim. Acta 1998, 81 932-982.
12. [2a] D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
13. [2b] E. Juaristi, D. Quintana, J. Escalante, Aldrichimica Acta 1994, 27, 3-11.
14. [2c] G. Cardillo, C. Tomasini, Chem. Soc. Rev. 1996, 117-128.
15. [2d] E. Juaristi, Enantioselective Synthesis of β-Amino Acids, Wiley-VCH, New York 1997.
16. E. Juaristi, D. Quintana, M. Balderas, E. Garcia-Pérez, Tetrahedron: Asymmetry 1996, 7, 2233-2246.
17. D. Seebach, A. Boog, W. B. Schweizer, Eur. J. Org. Chem. 1999, 335-360.
18. E. Arvanitis, H. Ernst, A. A. Ludwig, A. J. Robinson, P. B. Wyatt, J. Chem. Soc., Perkin Trans. 1 1998, 521-528.
19. R. Ponsinet, G. Chassaing, S. Lavielle, Tetrahedron: Asymmetry 1998, 9, 865-871.
20. [7a] H. Josien, A. Martin, G. Chassaing, Tetrahedron Lett. 1991, 32, 6547-6550.
21. [7b] H. Josien, G. Chassaing, Tetrahedron: Asymmetry 1992, 3, 1351-1354.
22. [8a] M. Ayoub, G. Chassaing, A. Loffet, S. Lavielle, Tetrahedron Lett. 1995, 36, 4069-4072.
23. [8b] M. Ayoub, Ph. D. Dissertation, Université P. et M. Curie, Paris, France, 1996.
24. Reviews: [9a] W. Oppolzer, Tetrahedron 1987, 43, 1969-2004.
25. [9b] W. Oppolzer, Pure Appl. Chem. 1990, 62, 1241-1250.
26. [9c] B. H. Kim, D. P. Curan, Tetrahedron 1993, 49, 293-318.
27. D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737-1739.
28. W. Oppolzer, R. Moretti, S. Thomi, Tetrahedron Lett. 1989, 30, 6009-6010.
29. R. Barrow, T. Hemscheidt, J. Liang, S. Paik, R. Moore, M. A. Tius, J. Am. Chem. Soc. 1995, 117, 2479-2490.
30. G. M. Salamonczyk, K. Han, Z. Guo, C. Sih, J. Org. Chem. 1996, 61, 6893-6900.
31. G. M. Sheldrick, SHELXS86, Program for the solution of crystal structures, Univ. of Göttingen, Federal Republic of Germany, 1986.
32. D. J. Watkin, C. K. Prout, R. J. Carruthers, P. Betteridge, CRYSTALS, Chemical Crystallography Laboratory, Oxford, U. K., 1996, issue 10.
33. D. T. Cromer, International Tables for X-Ray Crystallography, vol. IV, Kynoch Press, Birmingham, U. K., 1974.
34. J. R. Carruthers and D. J. Watkin, Acta Crystallogr. 1979, A35, 698-699.
35. D. J. Watkin, C. K. Prout, L. J. Pearce, CAMERON, Chemical Crystallography Laboratory, Oxford, U.K., 1996.