Chelated [3,3]-rearrangements of difluoroallylic alcohols

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5903-5906

  Broadhurst, M J ^b   Percy, J M ^a   Prime, M E ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOFLUORINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030858754     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01315-4     Document Type: Article

References (22)

1. For the best current collection of work in the area, see Ojima, I.; McCarthy, J. R.; Welch, J. T. Biomedical Frontiers of Fluorine Chemistry. In ACS Symposium Series; American Chemical Society: Washington DC, 1996; 639.
2. Percy, J. M. Contemp. Org.Synth. 1995, 4, 251-268.
3. Patel, S. T.; Percy, J. M.; Wilkes, R. D. Tetrahedron 1995, 51, 9201-9216.
4. Patel, S. T.; Percy, J. M.; Wilkes, R. D. J. Org. Chem. 1996, 61, 166-173.
5. Blades, K.; Patel, S. T.; Percy, J. M.; Wilkes, R. D. Tetrahedron Lett. 1996, 37, 6403-6406.
6. Patel, S. T.; Percy, J. M.; Wilkes, R. D. Tetrahedron 1995, 57, 11327-11336.
7. Examination of crystal structures of ester enolates showed that the α-elimination was incipient in the ground state, suggesting that these intermediates will be close to the limit of stability in solution; see Seebach, D.; Amstutz, R.; Laube, T.; Schweizer, W.B.; Dunitz, J.D. J. Am. Chem. Soc. 1985, 107, 5403-5409.
8. See Norley, M.; Kocienski, P.; Faller, A. Synlett 1996, 900-902 for a recent example. Also Panek, J. S.; Clark, T. D. J. Org. Chem. 1992, 57, 4323-4326 for earlier applications an d Oh, T.; Wrobel, Z.; Devine, P. N. Synlett 1992, 81-83 for a non-anionic version.
9. See Norley, M.; Kocienski, P.; Faller, A. Synlett 1996, 900-902 for a recent example. Also Panek, J. S.; Clark, T. D. J. Org. Chem. 1992, 57, 4323-4326 for earlier applications an d Oh, T.; Wrobel, Z.; Devine, P. N. Synlett 1992, 81-83 for a non-anionic version.
10. See Norley, M.; Kocienski, P.; Faller, A. Synlett 1996, 900-902 for a recent example. Also Panek, J. S.; Clark, T. D. J. Org. Chem. 1992, 57, 4323-4326 for earlier applications an d Oh, T.; Wrobel, Z.; Devine, P. N. Synlett 1992, 81-83 for a non-anionic version.
11. 19F NMR spectra of crude acids and ketoesters were essentially clean indicating that improvements in isolation methods should result in still higher isolated yields.
12. Hosangadi, B. D.; Dave, R. H. Tetrahedron Lett. 1996, 37, 6375-6378.
13. 4]+).
14. For recent examples, see Braun, M.; Vonderhagen, A.; Waldmuller, D. Liebigs Ann. 1995, 1447-1450; Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perezencabo, A. Synthesis 1996, 1070; Yoshida, M.; Suzuki, D.; Iyoda, M. Synth. Commun. 1996, 26, 2523-2529.
15. For recent examples, see Braun, M.; Vonderhagen, A.; Waldmuller, D. Liebigs Ann. 1995, 1447-1450; Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perezencabo, A. Synthesis 1996, 1070; Yoshida, M.; Suzuki, D.; Iyoda, M. Synth. Commun. 1996, 26, 2523-2529.
16. For recent examples, see Braun, M.; Vonderhagen, A.; Waldmuller, D. Liebigs Ann. 1995, 1447-1450; Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perezencabo, A. Synthesis 1996, 1070; Yoshida, M.; Suzuki, D.; Iyoda, M. Synth. Commun. 1996, 26, 2523-2529.
17. Howarth, J. A.; Owton, W. M.; Percy, J. M. J. Chem. Soc., Chem. Commun. 1995, 757-758.
18. Kuroboshi, M.; Ishihara, T. Bull. Chem. Soc. Jpn. 1990, 63, 428-437; Brigaud, T.; Doussot, P.; Portella, C. J. Chem. Soc., Chem. Commun. 1994, 2117-2118; Jin, F. Q.; Xu, Y. Y.; Huang, W. Y. J. Chem. Soc., Perkin Trans. 1 1993, 795-799; Kodama, Y.; Yamane, H.; Okumura, M.; Shiro, M.; Taguchi, T. Tetrahedron 1995, 51, 12217-12228.
19. Kuroboshi, M.; Ishihara, T. Bull. Chem. Soc. Jpn. 1990, 63, 428-437; Brigaud, T.; Doussot, P.; Portella, C. J. Chem. Soc., Chem. Commun. 1994, 2117-2118; Jin, F. Q.; Xu, Y. Y.; Huang, W. Y. J. Chem. Soc., Perkin Trans. 1 1993, 795-799; Kodama, Y.; Yamane, H.; Okumura, M.; Shiro, M.; Taguchi, T. Tetrahedron 1995, 51, 12217-12228.
20. Kuroboshi, M.; Ishihara, T. Bull. Chem. Soc. Jpn. 1990, 63, 428-437; Brigaud, T.; Doussot, P.; Portella, C. J. Chem. Soc., Chem. Commun. 1994, 2117-2118; Jin, F. Q.; Xu, Y. Y.; Huang, W. Y. J. Chem. Soc., Perkin Trans. 1 1993, 795-799; Kodama, Y.; Yamane, H.; Okumura, M.; Shiro, M.; Taguchi, T. Tetrahedron 1995, 51, 12217-12228.
21. Kuroboshi, M.; Ishihara, T. Bull. Chem. Soc. Jpn. 1990, 63, 428-437; Brigaud, T.; Doussot, P.; Portella, C. J. Chem. Soc., Chem. Commun. 1994, 2117-2118; Jin, F. Q.; Xu, Y. Y.; Huang, W. Y. J. Chem. Soc., Perkin Trans. 1 1993, 795-799; Kodama, Y.; Yamane, H.; Okumura, M.; Shiro, M.; Taguchi, T. Tetrahedron 1995, 51, 12217-12228.
22. cB elimination of fluorine atom would be suppressed by the presence of a π-donor substituent group at the acidic position, so it is possible that the dehydrofluorination is acid-catalysed.