Sequential Cross-Metathesis/ Electrophilic Fluorodesilylation: A Novel Entry to Functionalized Allylic Fluorides

Organic Letters

Volumn 5, Issue 25, 2003, Pages 4891-4893

  Thibaudeau, Sébastien ^a   Gouverneur, Véronique ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALLYL COMPOUND; ALLYLTRIMETHYLSILANE; FLUORIDE; FLUORINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CROSS METATHESIS; DESILYLATION; DRUG SYNTHESIS; FLUORODESILYLATION; METHODOLOGY;

EID: 0347683358     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035991a     Document Type: Article

References (25)

1. For general reviews on the physical properties of fluorinated compounds: (a) Smart, B. E. In Chemistry of Organic Fluorine Compounds II: A Critical Review; Hudlicky, M., Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995; pp 979-1010. (b) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Publishing Corp.: New York, 1994; pp 57-88. For applications of organofluorine compounds in pharmaceutical development, see, for example: (c) Edwards, P. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Publishing Corp.: New York, 1994; pp 501-541. (d) Ojima, I., McCarthy, J. R., Welch, J. T., Eds. Biomedical Frontiers of Fluorine Chemistry; ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996. (e) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley and Sons: New York, 1991.
2. For general reviews on the physical properties of fluorinated compounds: (a) Smart, B. E. In Chemistry of Organic Fluorine Compounds II: A Critical Review; Hudlicky, M., Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995; pp 979-1010. (b) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Publishing Corp.: New York, 1994; pp 57-88. For applications of organofluorine compounds in pharmaceutical development, see, for example: (c) Edwards, P. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Publishing Corp.: New York, 1994; pp 501-541. (d) Ojima, I., McCarthy, J. R., Welch, J. T., Eds. Biomedical Frontiers of Fluorine Chemistry; ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996. (e) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley and Sons: New York, 1991.
3. For general reviews on the physical properties of fluorinated compounds: (a) Smart, B. E. In Chemistry of Organic Fluorine Compounds II: A Critical Review; Hudlicky, M., Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995; pp 979-1010. (b) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Publishing Corp.: New York, 1994; pp 57-88. For applications of organofluorine compounds in pharmaceutical development, see, for example: (c) Edwards, P. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Publishing Corp.: New York, 1994; pp 501-541. (d) Ojima, I., McCarthy, J. R., Welch, J. T., Eds. Biomedical Frontiers of Fluorine Chemistry; ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996. (e) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley and Sons: New York, 1991.
4. For general reviews on the physical properties of fluorinated compounds: (a) Smart, B. E. In Chemistry of Organic Fluorine Compounds II: A Critical Review; Hudlicky, M., Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995; pp 979-1010. (b) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Publishing Corp.: New York, 1994; pp 57-88. For applications of organofluorine compounds in pharmaceutical development, see, for example: (c) Edwards, P. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Publishing Corp.: New York, 1994; pp 501-541. (d) Ojima, I., McCarthy, J. R., Welch, J. T., Eds. Biomedical Frontiers of Fluorine Chemistry; ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996. (e) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley and Sons: New York, 1991.
5. For general reviews on the physical properties of fluorinated compounds: (a) Smart, B. E. In Chemistry of Organic Fluorine Compounds II: A Critical Review; Hudlicky, M., Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995; pp 979-1010. (b) Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Publishing Corp.: New York, 1994; pp 57-88. For applications of organofluorine compounds in pharmaceutical development, see, for example: (c) Edwards, P. N. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Publishing Corp.: New York, 1994; pp 501-541. (d) Ojima, I., McCarthy, J. R., Welch, J. T., Eds. Biomedical Frontiers of Fluorine Chemistry; ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996. (e) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley and Sons: New York, 1991.
6. (a) Middleton, W. J., US Patent 3914265, 1975.
7. (b) Blackburn, G. M.; Kent, D. E. J. Chem. Soc., Chem. Commun. 1981, 511.
8. (c) Piva, O. Synlett 1994, 729.
9. (d) Grée, D. M.; Kermarrec, C. J. M.; Martelli, J. T.; Grée, R. L.; Lellouche, J.-P.; Toupet, L. J. J. Org. Chem. 1996, 61, 1918.
10. (e) Kermarrec, C. J. M.; Madiot, V.; Grée, D.; Meyer, A.; Gree, R Tetrahedron Lett. 1996, 61, 1918.
11. Kirihara, Masayuki; Kambayashi, Toshihiro; Momose, Takefumi Chem. Commun. 1996, 10, 1103.
12. Gouverneur, V.; Greedy, B. Chem. Eur. J. 2002, 8, 766.
13. Greedy, B.; Gouverneur, V. Chem. Commun. 2001, 233.
14. Greedy, B.; Paris, J.-M.; Vidal, T.; Gouverneur, V. Angew. Chem., Int. Ed. 2003, 42, 3291.
15. Seyferth, D.; Wursthorn, K. R.; Mammarella, R. E. J. Org. Chem. 1977, 42, 3104.
16. (b) Seyferth, D.; Wursthorn, K. R.; Lim, T. F. O.; Sepelak, D. J. J. Organomet. Chem. 1979, 181, 293.
17. (c) Fleming, I.; Paterson, I. Synthesis 1979, 446.
18. For general reviews on cross-metathesis: (a) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. For references on CM of allyltrimethylsilane, see, for example: (d) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117. (e) Bouzbouz, S.; De Lemos, E.; Cossy, J. Adv. Synth. Catal. 2002, 344, 627. (f) Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209.
19. For general reviews on cross-metathesis: (a) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. For references on CM of allyltrimethylsilane, see, for example: (d) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117. (e) Bouzbouz, S.; De Lemos, E.; Cossy, J. Adv. Synth. Catal. 2002, 344, 627. (f) Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209.
20. For general reviews on cross-metathesis: (a) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. For references on CM of allyltrimethylsilane, see, for example: (d) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117. (e) Bouzbouz, S.; De Lemos, E.; Cossy, J. Adv. Synth. Catal. 2002, 344, 627. (f) Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209.
21. For general reviews on cross-metathesis: (a) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. For references on CM of allyltrimethylsilane, see, for example: (d) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117. (e) Bouzbouz, S.; De Lemos, E.; Cossy, J. Adv. Synth. Catal. 2002, 344, 627. (f) Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209.
22. For general reviews on cross-metathesis: (a) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. For references on CM of allyltrimethylsilane, see, for example: (d) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117. (e) Bouzbouz, S.; De Lemos, E.; Cossy, J. Adv. Synth. Catal. 2002, 344, 627. (f) Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209.
23. For general reviews on cross-metathesis: (a) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. For references on CM of allyltrimethylsilane, see, for example: (d) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117. (e) Bouzbouz, S.; De Lemos, E.; Cossy, J. Adv. Synth. Catal. 2002, 344, 627. (f) Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209.
24. See for example: Vidari, G.; Lanfranchi, G.; Masciaga, F.; Moriggi, J.-D. Tetrahedron: Asymmetry 1996, 7, 3009.
25. Van Overmeire, I.; Boldin, S. A.; Venkatamaran, K.; Zisling, R.; De Jonghe, S.; Van Calenbergh, S.; De Keukeleire, D.; Futerman, A. H.; Herdewijn, P. J. Med. Chem. 2000, 43, 4189.