Ring expansion of N-acetyl aziridine-2-imides to oxazoline-4-imides, useful precursors of pure β-hydroxy α-aminoacids

Tetrahedron Letters

Volumn 38, Issue 39, 1997, Pages 6953-6956

  Cardillo, Giuliana ^a   Gentilucci, Luca ^a   Tolomelli, Alessandra ^a   Tomasini, Claudia ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYAMINO ACID; OXAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; ENANTIOMER; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030848014     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01630-4     Document Type: Article

References (20)

1. Choi, S. K.; Lee, J. S.; Kim, J. O.; Lee, W. K. J. Org. Chem. 1997, 62, 743, and references therein.
2. Tanner, D. Angew. Chem. Int. Ed 1994, 33, 599.
3. (a) Legters, J.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 16.
4. (b) Legters, J.; Willems, J. G. H.; Thijs, L.; Zwanenburg, B. Red. Trav. Chim. Pays-Bas 1992, 111, 59.
5. (c) Dauban, P.; Dubois, L.; Tran Huu Dau, M. E.; Dodd, R. H. J. Org. Chem. 1995, 60, 2035 and references therein.
6. Burnstein, I. J.; Fanta, P. E.; Green, B. S. J. Org. Chem. 1970, 35, 4084.
7. (a) Bates, S. G.; Varelas, M. A. Can. J. Chem. 1980, 58, 2562.
8. (b) Haidukewych, D.; Meyers, A. I. Tetrahedron Lett. 1972, 30, 3031.
9. Foglia, T. A.; Gregory, L. M.; Maerkel, G. J. Org. Chem. 1970, 35, 3779.
10. (a) Cardillo, G.; Gentilucci, L., Tomasini, C.; Visa Castejon-Bordas, M. P. Tetrahedron: Asymmetry 1996, 755.
11. (b) Cardillo, G.; Casolari, S.; Gentilucci, L.; Tomasini, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 1848.
12. 2), 3.90 (dq, J = 6.6, 8.7 Hz, 1H, CHMe), 4.89 (d, J = 2.7 Hz, 1H, COCH), 5.15 (d, J= 8.7 Hz, 1H, CHPh), 7.00-8.10 (m, 10H, Ph).
13. 2), 5.37 (d, J = 8.8 Hz, 1H, CHPh), 5.95 (d, J = 5.0 Hz, 1H, COCH), 7.10-8.20 (m, 10H, Ph).
14. Pines, S. H.; Kozlowski, M. A.; Karady, S. J. Org. Chem. 1969, 34, 1621.
15. 3).
16. While this work was in progress, Hori published his theoretical study: Hory, K.; Nishiguch T.; Nabeja, A. J. Org. Chem. 1997, 62, 3081.
17. Gage, J. R.; Evans, D. A. Org. Synthesis 1989, 68, 83.
18. D= +12 (c 4.7, MeOH).
19. D= -13 (c 5.0, 5N HCl).
20. 7a