Regioselective opening of 3-substituted N-ethoxycarbonyl aziridine-2-carboxylates with metal halides toward the preparation of α and β-amino acids

Tetrahedron Letters

Volumn 37, Issue 38, 1996, Pages 6893-6896

  Righi, Giuliana ^a   D'Achille, Raffaella ^a   Bonini, Carlo ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF BASILICATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BETA AMINO ACID;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030590413     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01509-2     Document Type: Article

References (20)

1. 1. See review Tanner, D. Angew. Chem. Int. Ed. Engl. 1994, 33, 599-619.
2. 2. a) Tanner, D.; Somfai, P. Tetrahedron 1988, 44, 619-624.
3. b) Tanner, D.; He, H. M.; ibidem 1992, 48, 6079.
4. c) Tanner, D.; Gautun, O. R.; ibidem 1995, 51, 8279-8288.
5. 3. Legters, J.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 1-15.
6. 4. a) Legters, J.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 16-21.
7. b) Legters, J.; Willems, J. G. H.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 59-68.
8. 5. Tanner, D. ; Birgersson, C. ; Dhaliwal, H. K. Tetrahedron Lett. 1990, 31, 1903-1906.
9. 6. Bonini, C.; Righi, G.; Rumboldt, G. Tetrahedron 1995, 51, 13401-13407.
10. 7. Bonini, C.; Righi, G.; Rumboldt, G. J. Org. Chem. 1996, 61, 3557-3560.
11. 3 by flash-chromatography.
12. 1H-NMR analysis.
13. 1H-NMR analysis.
14. 11. See review Bonini, C. ; Righi, G. Synthesis 1994, 225-238.
15. 12. Details of the radical reduction and subsequent hydrolysis to the amino acids will be given in a forthcoming full paper.
16. 13. Yun Gao, Hanson, R. M. ; Klunder, J. M. ; Ko, S. Y. ; Masamune, H. ; Sharpless, K. B. J. Am. Chem Soc. 1987, 109, 5765-5780.
17. 14. Bunnage M.E., Burke A.J., Davies S.G., Goodwin C.J. Tetrahedron: Asymmetry 1995, 6, 165-176.
18. 15. a) Evans, F. A. ; Faul, M.M. ; Bilodeau, M. T. ; Anderson, B. A. ; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328-5329.
19. b) Davis, F. A. ; Zhou, P. ; Reddy, G. V. J. Org. Chem. 1994, 59, 3243-3245.
20. c) Lim, Y. ; Lee, W. K. Tetrahedron Lett. 1995, 36, 8431-8434.