New base induced rearrangements of 4-acylisoxazolidines. Anionic reactional cascades from five membered rings to either four membered rings or open chain compounds

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 917-920

  Gandolfi, Remo ^a   Gamba, Anna ^a   Presutto, Milena ^a   Oberti, Roberta ^b   Sardone, Nicola ^b  

^a UNIVERSITY OF PAVIA   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ISOXAZOLIDINE DERIVATIVE; MALONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030060796     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02279-1     Document Type: Article

References (16)

1. Grünanger, P.; Vita-finzi, P. Isoxazoles , Wiley-Interscience, New York 1991, ch 3.
2. (a) Joucla, M.; Hamelin, J.; Carrie', R. Tetrahedron, 1974, 30, 1121-1126.
3. (b) Padwa, A.; Koehler, K. F.; Rodriguez, A. J. Org. Chem., 1984, 49, 282-288.
4. (c) Cordero, F. M.; Brandi, A.; De Sarlo, F.; Viti, G. J. Chem. Soc., Chem. Commun., 1994, 1047.
5. (d) Gandolfi, R., Unpublished results.
6. For base induced opening of isoxazolidinium salts see reference 1 and Casuscelli, F.; Chiacchio, U.; Rescifina, A.; Romeo, R.; Romeo, G.; Tommasini, S.; Uccella, N. Tetrahedron, 1995, 51, 2979-2990.
7. Burdisso, M.; Gandolfi, R.; Grünanger, P. Tetrahedron, 1989, 45, 5579-5594.
8. Similar results were obtained by using sodium methoxide as base in methanol (r.t., 24 h).
9. 8
10. +·), 191 (83%). Very similar spectroscopic data were exhibited by 2c (yellow needles from MeOH, m.p. 160-162°C) and 2d. (yellow needles from MeOH, m.p. 139-140°C).
11. 2O, m.p. 167-169°C).
12. 3-C = -3.9.
13. Kemp, D. S.; Vellaccio, F. Organic Chemistry, Worth publishers, New York, 1980, pp 301 and 365.
14. Reference 1, p. 310.
15. We thank A. Vasella (Friburg University, Switzerland) for helpful suggestions about this mechanism.
16. Smith, J. G.; Simpson, G. E. F. J. Org. Chem. 1976, 41, 2878-2881.