Synthesis of α-fluoro-β,γ-alkenylphosphonates and conjugated fluoroenynes from a common intermediate (α-fluoropropargyl) phosphonate

Tetrahedron

Volumn 54, Issue 51, 1998, Pages 15541-15554

  Benayoud, Farid ^a   Chen, Ling ^a   Moniz, George A ^a   Zapata, Antonio J ^a,b   Hammond, Gerald B ^a  

^a UNIVERSITY OF MASSACHUSETTS DARTMOUTH   (United States)

^b UNIVERSIDAD SIMÓN BOLÍVAR   (Venezuela)

Author keywords

Fluoroenynes; Fluorophosphonates; Hydrogenation; Olefination

Indexed keywords

ALKENYL GROUP; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; FLUORINATION; HYDROGENATION; MOLECULAR INTERACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032542174     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01017-5     Document Type: Article

References (40)

1. (1) Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; American Chemical Society: Washington DC, 1996; Vol. 639.
2. (2) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; Wiley Interscience: New York, 1991.
3. (3) Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; American Chemical Society: Washington DC, 1991; Vol. 456.
4. (4) Fluorine-containing Molecules. Structure, Reactivity, Synthesis, and Applications; Liebman, J. F.; Greenberg, A.; Dolbier, W. R., Eds.; VCH Publishers, Inc.: New York, 1988.
5. (5) O'Hagan, D.; Rzepa, H. S. J. C. S. Chem. Commun. 1997, 645-652.
6. (6) Percy, J. M.; Wilkes, R. D. Tetrahedron 1997, 53, 14749-14762.
7. (7) Benayoud, F.; deMendonca, D. J.; Digits, C. A.; Moniz, G. A.; Sanders, T. C.; Hammond, G. B. J. Org. Chem. 1996, 61, 5159-5164.
8. (8) Benayoud, F.; Hammond, G. B. J. C. S. Chem. Commun, 1996, 1447-1448.
9. (9) Megati, S.; Phadtare, S.; Zemlicka, J. J. Org. Chem 1992, 57, 2320-2327.
10. (10) Haraden, M. R.; Parkin, A.; Parratt, M. J.; Perkins, R. M. J. Med. Chem 1993, 36, 1343-1355.
11. (11) Perez-Perez, M.-J.; Balzarini, J.; Rozenski, J.; DeClercq, E.; Herdewijn, P. Bioorg. & Med. Chem. Letters 1995, 5, 1115-1118.
12. (12) Halazy, S.; Gross-Beiges, V. J. Chem. Soc., Chem. Commun. 1992, 743-745.
13. (13) Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763-2764.
14. (14) Xu, Z.-Q.; Zemlicka, J. Tetrahedron 1997, 53, 5389-5396.
15. (15) Yokomatsu, T.; Suemune, K.; Murano, T.; Shibuya, S. J. Org. Chem. 1996, 61, 7207-7211 and references therein.
16. (16) Sanders, T. C.; Hammond, G. B. J. Org. Chem. 1993, 5598-5599.
17. (17) Zhang, X.; Qiu, W.; Burton, D. J. In 13th Winter Fluorine Conference St. Petersburg Beach, Florida, 1997.
18. (18) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518.
19. (19) Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103-2117.
20. (20) Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry, Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, Germany, 1995, p 203-283.
21. (21) Dare, S.; Ducroix, B.; Bernard, S.; Nicholas, K. M. Tetrahedron Lett. 1996, 37, 4341-4344.
22. (22) Melikyan, G. G.; Vostrowsky, O.; Bauer, W.; Bestmann, H. J.; Khan, M.; Nicholas, K. M. J. Org. Chem. 1994, 59, 222-229.
23. (23) Yang, Z. Y.; Burton, D. J. Tetrahedron Lett. 1990, 31, 1369-1372.
24. (24) Yang, Z. Y.; Burton, D. J. J. Fluorine Chem. 1991, 53, 307-326.
25. (25) Ichikawa, J.; Ikeura, C; Minami, T. J. Fluorine Chem. 1993, 63, 281-285.
26. (26) Camps, F.; Coll, J.; Fabrias, G.; Guerrero, A.; Riba, M. Experientia 1984, 40, 933-934.
27. (27) Eddarir, S.; Francesch, C.; Mestdagh, H.; Rolando, C. Tetrahedron Lett. 1990, 31, 4449-4452.
28. (28) Blackburn, G. M.; Parratt, M. J. J. Chem. Soc. Perkin I 1986, 1425-1430.
29. (29) Obayashi, M.; Ito, E.; Matsui, K.; Kondo, K. Tetrahedron Lett. 1982, 23, 2323-2326.
30. (30) Sanders, T. C.; Golen, J. A.; Williard, P. G.; Hammond, G. B. J. Fluorine Chem. 1997, 85, 173-175.
31. (31) Schmidt, H. M.; Arens, J. F. Recueil Trav. Chim. Pays-Bas 1967, 86, 1138-1142.
32. (32) Sun, W.-C.; Prestwich, G. D. Tetrahedron Letters 1990, 31, 801-804.
33. (33) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
34. (34) Koskinen, A. M. P.; Koskinen, P. M. Synlett 1993, 501-502.
35. (35) Paterson, I.; Yeung, K.-S.; Smaill, J. B. Synlett 1993, 774-776.
36. (36) Bonadies, F.; Cardilli, A.; Lattanzi, A.; Orelli, L. R.; Scettri, A. Tetrahedron Lett. 1994, 35, 3383-3386.
37. (37) Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183-2186.
38. (38) Furuta, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768-2776.
39. (39) Differding, E.; Duthaler, R. O.; Krieger, A.; Rueegg, G. M.; Schmit, C. Synlett 1991, 395-396.
40. (40) Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405-4408.