A new, mild, and efficient synthesis of 2,2-difluoro-3-hydroxyacids through a selective haloform reaction

Journal of Organic Chemistry

Volumn 70, Issue 26, 2005, Pages 10883-10885

  Jimenez O ^a   Bosch, M P ^b   Guerrero, A ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; FLUORINE; KETONES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

2,2-DIFLUORO-3-HYDROXYACIDS; PENTAFLUOROENOLATE; REACTION SEQUENCE;

ORGANIC ACIDS;

2,2 DIFLUORO 3 HYDROXYACID; ALDEHYDE; FLUORINE; HEXAFLUORO 2 PROPANOL; HYDROXYACID; KETONE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 29944434270     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0518856     Document Type: Article

References (36)

1. (a) Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Chemistry: Principles and Commercial Applications; Plenum Press: New Yrok, 1994.
2. (b) Filler, R.; Kobayashi, Y.; Yagupolskii, L. M. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Elsevier Science: Amsterdam, 1993.
3. (a) Hudlicky, M. In Chemistry of Organic Fluorine Compounds; 2nd ed.; Horwood, E., Mellor, J., Eds.; Ellis Horwood and PTR Prentice Hall: New York, 1992.
4. (b) Kukhar, V. P.; Soloshonok, V. A. Fluorine-Containing Amino Acids; John Wiley & Sons: Chichester, 1995.
5. (a) Biomedical Frontiers of Fluorine Chemistry; Ojima, L., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, DC, 1996.
6. (b) Ojima, I. ChemBioChem 2004, 5, 628.
7. (a) Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1813.
8. (b) Ashour, M.-B. A.; Hammock, B. D. Biochem. Pharm. 1987, 36, 1869.
9. (c) Street, I. P.; Lin, H. K.; Laliberté, F.; Ghomashchi, F.; Wang, Z.; Perrier, H.; Tremblay, N. M.; Huang, Z.; Weech, P. K.; Gelb, M. H. Biochemistry 1993, 32, 5935.
10. (d) Guerrero, A.; Rosell, G. Curr. Med. Chem. 2005, 12, 461.
11. Fukuda, H.; Tetsu, M.; Kitazume, T. Tetrahedron 1996, 52, 157.
12. Saxty, B. A.; Novelli, R.; Dolle, R. E.; Kruse, L. I.; Reid, D. G.; Camilleri, P.; Wells, T. N. C. Eur. J. Biochem. 1991, 202, 889.
13. Brunt, R. V.; Eisenthal, R.; Symons, S. A. FEBS Lett. 1971, 13, 89.
14. (a) Thaisrivongs, S.; Pals, D. T.; Kati, W. M.; Turner, S. R.; Thomasco, L. M.; Watt, W. J. Med. Chem. 1986, 29, 2080.
15. (b) Karen, F.; Spaltenstein, A.; Hopkins, P. B.; Gelb, M. H. J. Med. Chem. 1987, 30, 1617.
16. Rando, R. R. U.S. Patent 6,015,877, 1996.
17. Itoh, K.; Takeda, M.; Namekawa, M.; Nayuri, S.; Murayama, Y.; Yamazaki, T.; Kitazume, T. Ferroelectrics 1993, 148, 85.
18. (a) Ocampo, R.; Dolbier, W. R., Jr.; Bartberger, M. D.; Paredes, R. J. Org. Chem. 1997, 62, 109.
19. (b) Mochizuki, N.; Oota, H.; Sukai, T. Japanese Patent 06253889, 1994.
20. (c) Thaisrivongs, S.; Pals, D. T.; Kati, W. M.; Turner, S. R.; Thomasco, L. M. J. Med. Chem. 1985, 28, 1553.
21. (a) Durán, I.; Parrilla, A.; Feixas, J.; Guerrero, A. Bioorg. Med. Chem. Lett. 1993, 3, 2593.
22. (b) Parrilla, A.; Guerrero, A. Chem. Senses 1994, 19, 1.
23. (c) Renou, M.; Lucas, P.; Malo, E.; Quero, C.; Guerrero, A. Chem. Senses 1997, 22, 407.
24. (d) Bau, J.; Martínez, D.; Renou, M.; Guerrero, A. Chem. Senses 1999, 24, 473.
25. (e) Jiménez, O.; Bosch, M. P.; Guerrero, A. Synthesis 2000, 1917.
26. (f) Riba, M.; Sans, A.; Bau, P.; Grolleau, G.; Renou, M.; Guerrero, A. J. Chem. Ecol. 2001, 27, 1879.
27. (g) Quero, C.; Rosell, G.; Jiménez, O.; Rodriguez, S.; Bosch, M. P.; Guerrero, A. Bioorg. Med. Chem. 2003, 11, 1047.
28. (h) Rosell, G.; Herrero, S.; Guerrero, A. Biochem. Biophys. Res. Commun. 1996, 226, 287.
29. Qian, C.-P.; Nakai, T. Tetrahedron Lett. 1988, 29, 4119.
30. Qian, C.-P.; Nakai, T. In Selective Fluorination of Organic and Bioorganic Chemistry; Welch, J. T., Ed.; ACS Symposium Series; American Chemical Society: Washington, DC, 1991; Vol. 456, p 82.
31. Olivella, S.; Solé, A.; Jiménez, O.; Bosch, M. P.; Guerrero, A. J. Am. Chem. Soc. 2005, 127, 2620.
32. Simmons, J. H.; Rammler, E. O. J. Am. Chem. Soc. 1943, 65, 389.
33. (a) Magnus, N. A.; Confalone, P. N.; Storace, L. Tetrahedron Lett. 2000, 41, 3015.
34. (b) Yang, D.; Wong, M.-K.; Z., Y. J. Org. Chem. 2000, 65, 4179.
35. (c) Scheuring, J.; Kugelbrey, K.; Weinkauf, S.; Cushman, M.; Bacher, A.; Fischer, M. J. Org. Chem. 2001, 66, 3811.
36. (d) Narita, T.; Hagiwara, T.; Hamana, H.; Tomooka, K.; Liu, Y.-Z.; Nakai, T. Tetrahedron Lett. 1995, 36, 6091.