(S(s)-5-ethoxy-3-p-tolylsulfinylfuran-2(5H)-ones as chiral dipolarophiles: First asymmetric cycloaddition of diazomethane to vinyl sulfoxides

Tetrahedron Asymmetry

Volumn 7, Issue 7, 1996, Pages 1943-1950

  García Ruano, Jose L ^a   Fraile, Alberto ^a   Martín, M Rosario ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; PYRAZOLE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030200961     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00233-9     Document Type: Article

References (26)

1. 1. Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760 and references cited therein.
2. 2. Carreño, M. C.; Garcia Ruano, J. L., Toledo, M. A.; Urbano, A.; Remor, C. Z.; Stefani, W.; Fischer, J. J. Org. Chem. 1996, 61, 503-509 and references cited therein.
3. 3. Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T. Tetrahedron: Asymmetry 1991, 2, 1379-1390.
4. b) Louis, C., Hootelé, C. Tetrahedron: Asymmetry 1995, 6, 2149-2152.
5. c) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli, A. Tetrahedron: Asymmetry 1993, 4, 2131-2134.
6. d) Takahashi, T.; Kitano, K.; Hagi, T.; Nihonmatsu, H.; Koizumi, T. Chem. Lett. 1989, 597-598.
7. e) Chaigne, F.; Gotteland, J.; Malacria, M. Tetrahedron Lett. 1989, 30, 1803-1806.
8. f) Koizumi, T.; Hirai, H.; Yoshii, E. J. Org. Chem. 1982, 47, 4004-4005.
9. g) Bravo, P.; Bruché, L.; Diliddo, D.; Resnati, G.; J. Chem. Research (S). 1993, 346-347.
10. 4. Only two reports dealing with the addition of diazomethane to racemic vinyl sulfoxides have been reported (Dean, F. M.; Park, B. K. Tetrahedron Lett. 1974, 4275-4277; Padwa, A.; Meske, M; Rodriguez, A. Heterocycles 1995, 40, 191-204) in which the sulfinylpyrazolines were not isolated.
11. 4. Only two reports dealing with the addition of diazomethane to racemic vinyl sulfoxides have been reported (Dean, F. M.; Park, B. K. Tetrahedron Lett. 1974, 4275-4277; Padwa, A.; Meske, M; Rodriguez, A. Heterocycles 1995, 40, 191-204) in which the sulfinylpyrazolines were not isolated.
12. 5. a) Fariña, F.; Martín, M. R.; Martín, M. V.; Martinez, A. Heterocycles 1994, 38, 1307-1316. and references cited therein
13. b) Fariña, F.; Martín, M. V.; Soria, M. L. An. Quim. 1995, 91, 65-73.
14. 6. Fariña, F.; Martín, M. V.; Sanchez, F. Heterocycles 1986, 24, 2587-2592
15. 7. a) de Lange, B.; Feringa, B. L. Tetrahedron Lett. 1988, 29, 5317-5320.
16. b) Keller, E.; de Lange, B.; Rispens, M. T.; Feringa, B. L. Tetrahedron 1993, 49, 8899-8910.
17. 8. Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Reapath, J. Tetrahedron 1995, 51, 7791-7808.
18. 9. Reed, A. D.; Hegedus, L. S. J. Org. Chem. 1995, 60, 3787-3794
19. 10. Carretero, J. C.; García Ruano, J. L.; Lorente, A.; Yuste, F. Tetrahedron: Asymmetry 1993, 4, 177-180.
20. 11. Feringa, B. L.; de Lange, B.; de Jong, J. C. J. Org: Chem. 1989, 54, 24712475
21. 12. During the preparation of this manuscript a new reaction of racemic vinyl sulfoxides with diazomethane has been reported (Plancquaert, M.; Redon, M.; Janousek, Z.; Viehe, H. G. Tetrahedron 1996, 52, 4383-4396). This is the first paper containing NMR data of the racemic sulfinylpyrazolines.
22. 13. As a consequence of the high stability of this sulfinylpyrazolines, 2a and 2b can be easily separated by chromatography. This separation is much easier than that of the furanones 1a and 1b, and therefore, reaction of the 1a + 1b mixture with diazomethane and further separation of the obtained pyrazolines, allowed higher yields of 2a and 2b (see experimental).
23. 14. Hanessian, S.; Murray, P. J. J. Org. Chem. 1987. 52, 1170-1172.
24. 15. Thermally induced extrusion of nitrogen from 3H, 4H, 3a,6a-dihydrofuro[3,4-c]pyrazol-6-ones is a known method to obtain 4-methylfuran-2(5H)-ones (Jefford, C. W.; Sledeski, A.; Boukouvalas, J. Helv. Chim. Acta 1989, 72, 1362-1370 and Ortuño, R. M.; Bigorra, J.; Font, J. Tetrahedron 1987, 43, 2199-2202 and reference 13).
25. 15. Thermally induced extrusion of nitrogen from 3H, 4H, 3a,6a-dihydrofuro[3,4-c]pyrazol-6-ones is a known method to obtain 4-methylfuran-2(5H)-ones (Jefford, C. W.; Sledeski, A.; Boukouvalas, J. Helv. Chim. Acta 1989, 72, 1362-1370 and Ortuño, R. M.; Bigorra, J.; Font, J. Tetrahedron 1987, 43, 2199-2202 and reference 13).
26. 16. The steric interactions of diene with the substituents at C-5 are more restrictive than those of the diazomethane with such substituents. (Table presented)