Fluoro alcohol as reaction medium: One-pot synthesis of β-hydroxy sulfoxides from epoxides

Tetrahedron Letters

Volumn 41, Issue 16, 2000, Pages 2895-2898

  Kesavan, Venkitasamy ^a   Bonnet Delpon, Danièle ^a   Bégué, Jean Pierre ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; ALCOHOL; EPOXIDE; ETHYLENE OXIDE; FLUORINATED HYDROCARBON; SULFOXIDE;

ARTICLE; HYDROGEN BOND; OXIDATION; PYROLYSIS; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034655862     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00305-1     Document Type: Article

References (27)

1. (a) Lidy, W.; Sundermeyer, W. Tetrahedron Lett. 1973, 14, 1449-1452.
2. (b) Mullis, J. C.; Weber, W. P. J. Org. Chem. 1983, 47, 2873-2876.
3. (c) Blandy, C.; Choukroun, T. L.; Gervais, D. Tetrahedron Lett. 1983, 47, 2873-2876.
4. (d) Guddenheim, T. L. J. Am. Chem. Soc. 1982, 104, 5849-5851.
5. (e) Gassman, P. G.; Gremban, R. S. Tetrahedron Lett. 1984, 25, 3259-3262.
6. (f) Babu, M. H.; Frei, B. Helv. Chim. Acta 1986, 69, 415-422.
7. (g) Sinou, D.; Emziane, M. Tetrahedron Lett. 1986, 27, 4423-4426.
8. (a) Conte, V.; Di Furia, F.; Licini, G.; Modena, G.; Sbampto, G.; Valle, G. Tetrahedron Asymmetry 1991, 2, 257-268.
9. (b) Solladie, G.; Almario, A.; Dominguez, C. Pure. Appl. Chem. 1994, 66, 2159-2175
10. (c) Gabbi, C.; Ghelfi, F.; Grandi, R. Synth. Commun. 1997, 27, 2857-2863 and references cited therein.
11. (a) Trost, B. M. In Organic Sulfur Chemistry; Stirling, C. J. M., Ed.; Butterworths: London, 1975; p. 237.
12. (b) Trost, B. M. Acc. Chem. Soc. 1978, 11, 453-461.
13. (a) Corey, E. J.; Clark, D. A.; Goto, G.; Marfat, A.; Mioskowski, C.; Samuelsson, B.; Hammarstrom, S. J. Am. Chem. Soc. 1980, 102, 1436-1438.
14. (b) ibid 1980, 102, 3663-3665.
15. (a) Corey, E. J.; Clark, D. A.; Marfat, A.; Goto, G. Tetrahedron Lett. 1980, 21, 3143-3146.
16. (b) Peach, M. E. In The Chemistry of the Thiol Group; Patai, S., Ed.; John Wiley: New York, 1974; Part 3, p. 771.
17. (a) Vougioukas, A. E.; Kagan, H. B. Tetrahedron Lett. 1987, 28, 6065-6068.
18. (b) Iqbal, J.; Pandey, A.; Shukla, A.; Srivastava, R. R.; Tripathi, S. Tetrahedron 1990, 18, 6423-6432.
19. (c) Chini, M.; Crotti, P.; Giovani, E.; Macchia, F.; Pineschi, M. Synlett 1992, 303-305.
20. Posner, G. H.; Rogers, D. Z. J. Am. Chem. Soc. 1977, 99, 8208-8214.
21. (a) Ravikumar, K. S.; Barbier, F.; Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron 1998, 54, 7457-7460.
22. (b) Ravikumar, K. S.; Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141-3144.
23. (b) Ravikumar, K. S.; Zhang, Y. M.; Bégué, J. P.; Bonnet-Delpon, D. Eur. J. Org. Chem. 1998, 2937-2940.
24. (c) Ravikumar, K. S.; Barbier, F.; Bégué, J. P.; Bonnet-Delpon, D. J. Fluorine Chem. 1999, 95, 123-125.
25. Kesavan, V.; Bonnet-Delpon, D.; Bégué, J. P. Synthesis, in press.
26. 1H NMR (400 MHz) major isomer (1S*, 2S7z.ast;, (S) S*): 1.0-1.45 (m, 5H), 1.70 (m, 2H), 2.10 (m, 1H), 2.74 (ddd, J=12.5, 9.5, 4.5 Hz, 1H, CH-SO), 4.12 (1H, td, J=9.5, 4.9 Hz, 1H, CH-OH), 7.5 (m, 3H), 7.7 (m, 2H); minor isomer (1S*, 2S*, (S) R*): 1.0-1.45 (m, 5H), 1.70 (m, 2H), 2.10 (m, 1H), 2.68 (ddd, J=12.5, 10.5, 4 Hz, 1H, CH-SO), 3.9 (td, J=10.5, 5 Hz, 1H, CH-OH), 7.5 (m, 3H), 7.7 (m, 2H). Crystallisation from acetone afforded pure (1S7z.ast;, 2S*, (S) S*) isomer: mp 154-155°C (Ref. 11, 156-157°C).
27. Carreno, M. C.; Ruano, J. L.; Martin, A. M.; Padregal, C.; Rodriguez, R. A.; Rubio, A.; Sanchez, J.; Solladié, G. J. Org. Chem. 1990, 55, 2120-2128.