Diastereoreactivity of a chiral oxathiane derived from 5-hydroxy-1-tetralone

European Journal of Organic Chemistry

Volumn , Issue 2, 2003, Pages 337-345

  Solladié Cavallo, Arlette ^a   Balaz, Milan ^a   Salisova, Marta ^b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b Faculty of Natural Sciences   (Slovakia)

Author keywords

1,3 Oxathiane; Diastereoreactivity; Lithiation

Indexed keywords

1,3 OXATHIANE DERIVATIVE; 5 HYDROXY 1 TETRALONE; CARBONYL DERIVATIVE; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; CONFORMATION; DIASTEREOISOMER; GRIGNARD REACTION; LITHIATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037245010     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390039     Document Type: Article

References (24)

1. E. L. Eliel, J. K. Koskimies, B. Lohri, J. Am. Chem. Soc. 1978, 100, 1614.
2. E. L. Eliel, W. J. Frazee, J. Org. Chem. 1979, 44, 3598.
3. F. Martinez-Ramos, M. E. Vargas-Diaz, L. Chacon-Garcia, J. Tamariz, P. Joseph-Nathan, L. G. Zepeda, Tetrahedron: Asymmetry 2001, 12, 3095.
4. J. E. Lynch, E. L. Eliel, J. Am. Chem. Soc. 1984, 106, 2943.
5. A. Solladié-Cavallo, A. Adib, Tetrahedron 1992, 48, 2453.
6. [6a] A. Solladié-Cavallo, A. Diep-Vohuule, J. Org. Chem. 1995, 60, 3494.
7. [6b] A. Solladié-Cavallo, A. Diep-Vohuule, V. Sunjic, V. Vinkovic, Tetrahedron: Asymmetry 1996, 7, 1783.
8. A. Solladié-Cavallo, A. Diep-Vohuule, T. Isarno, Angew. Chem. Int. Ed. 1998, 37, 1689.
9. As an example, compound I, isolated upon hydrolysis of oxathiane derivatives 4, can be retransformed into the desired starting oxathiane
10. A. Solladié-Cavallo, M. Balaz, M. Salisova, C. Suteu, L. Nafie, X. Cao, T. B. Freedman, Tetrahedron: Asymmetry 2001, 12, 2605.
11. E. L. Eliel, S. Morris-Natschke, J. Am. Chem. Soc. 1984, 106, 2937.
12. E. L. Eliel, A. A. Hartmann, A. G. Abatjoglou, J. Am. Chem. Soc. 1974, 96, 1807.
13. R. Amstutz, D. Seebach, P. Seiler, B. Schweizer, J. D. Dunitz, Angew. Chem. Int. Ed. Engl. 1980, 19, 53.
14. D. Seebach, J. Gabriel, R. Hässig, Helv. Chim. Acta 1984, 67, 1083.
15. W. Bauer, D. Seebach, Helv. Chim. Acta 1984, 67, 1972.
16. H. J. Reich, J. P. Borst, R. R. Dykstra, Tetrahedron 1994, 50, 5869.
17. E. L. Eliel, X. Bai, A. F. Abdel-Magid, R. O. Hutchins, J. Org. Chem. 1990, 50, 4951.
18. J. Wei, R. O. Hutchins, J. Prol, Jr., J. Org. Chem. 1993, 58, 2920.
19. S. V. Frye, E. L. Eliel, J. Am. Chem. Soc. 1988, 110, 484.
20. K. Y. Ko, W. J. Frazee, E. L. Eliel, Tetrahedron 1984, 40, 1333.
21. K. Fuji, M. Ueda, K. Sumi, E. Fujita, J. Org. Chem. 1985, 50, 662.
22. R. Bellato, A. Gatti, P. Venturello, Tetrahedron 1992, 48, 2501.
23. H. Perrier, G. Huyer, R. N. Young, Tetrahedron Lett. 1992, 33, 725.
24. N. Watanabe, H. Kobayashi, M. Azami, M. Matsumoto, Tetrahedron 1999, 55, 6831.