Synthesis and Horner-Wittig chemistry of (fluoromethyl)diphenylphosphane oxide

European Journal of Organic Chemistry

Volumn , Issue 5, 2001, Pages 897-910

  Van Steenis, Jan Hein ^a   Van Der Gen, Arne ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

DAST; Fluorine; Fluoro olefins; Horner Wittig reaction; Phosphane oxide

Indexed keywords

(BENZYL)(PHENYL)PHOSPHINIC FLUORIDE; (DIPHENYLPHOSPHINOYL)METHYL 4 TOLUENESULFONATE; (FLUOROMETHYL)DIPHENYLPHOSPHANE OXIDE; ALDEHYDE; ALKENE DERIVATIVE; BASE; CARBONYL DERIVATIVE; FLUORIDE; KETONE; PHOSPHORUS DERIVATIVE; POTASSIUM FLUORIDE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

EID: 0035112236     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200103)2001:5<897::aid-ejoc897>3.0.co;2-b     Document Type: Article

References (58)

1. D. J. Burton, Z.-Y. Yang, W. Qiu, Chem. Rev. 1996, 96, 1641-1715.
2. S. Hayashi, T. Nakai, N. Ishikawa, D. J. Burton, D. G. Naae, H. S. Kesling, Chem. Lett. 1979, 983-986.
3. M. L. Edwards, D. M. Stemerick, E. T. Jarvi, D. P. Matthews, J. R. McCarthy, Tetrahedron Lett. 1990, 31, 5571-5574.
4. J. R. McCarthy, D. P. Matthews, M. L. Edwards, D. M. Stemerick, E. T. Jarvi, Tetrahedron Lett. 1990, 31, 5449-5452.
5. [5a] J. R. McCarthy, D. P. Matthews, D. M. Stemerick, E. W. Huber, P. Bey, B. J. Lippert, R. D. Snyder, P. S. Sunkara, J. Am. Chem. Soc. 1991, 113, 7439-7440.
6. [5b] A. P. Khrimian, A. B. DeMilo, R. M. Waters, N. J. Liquido, J. M. Nicholson, J. Org. Chem. 1994, 59, 8034-8039.
7. [5c] J. R. McCarthy, D. P. Matthews, J. P. Paolini, Org. Synth. 1995, 72, 216-224.
8. [5d] J. R. McCarthy, E. W. Huber, T.-B. Le, M. Laskovics, D. P. Matthews, Tetrahedron 1996, 52, 45-58.
9. [6a] M. Schlosser, M. Zimmermann, Synthesis 1969, 75-76.
10. [6b] F. Manfré, J. M. Kern, J.-F. Biellmann, J. Org. Chem. 1992, 57, 2060-2065.
11. [6c] Q. Wang, H.-x. Wei, M. Schlosser, Eur. J. Org. Chem. 1999, 3263-3268.
12. [6d] D. J. Burton, P. E. Greenlimb, III, J. Org. Chem. 1975, 40, 2796-2801.
13. [6e] Z. Du, M. J. Haglund, L. A. Pratt, K. L. Erickson, J. Org. Chem. 1998, 63, 8880-8887.
14. [6f] M. El-Khoury, Q. Wang, M. Schlosser, Tetrahedron Lett. 1996, 37, 9047-9050.
15. D. G. Cox, N. Gurusamy, D. J. Burton, J. Am. Chem. Soc. 1985, 107, 2811-2812.
16. [8a] R. Waschbüsch, J. Carran, A. Marinetti, P. Savignac, Synthesis 1997, 727-743; and references therein.
17. [8b] A. P. Tomilov, B. I. Martynov, Yu. D. Smirnov, F. M. Semchenko, J. Fluorine Chem. 1997, 82, 39-41.
18. [8c] C. J. Hamilton, S. M. Roberts, J. Chem. Soc., Perkin Trans. 1 1999, 1051-1056.
19. G. M. Blackburn, M. J. Parratt, J. Chem. Soc., Chem. Commun. 1983, 886-888.
20. For the use of "phosphane" instead of "phosphine", see IUPAC recommendations: G. P. Moss, P. A. S. Smith, D. Tavernier, Pure Appl. Chem. 1995, 67, 1307-1375.
21. W. Wegener, Z. Chem. 1971, 11, 262.
22. [13]
23. P. P. de Wit, Ph. D. Dissertation, Leiden University, 1987.
24. E. D. Bergmann, I. Shahak, Chem. Ind. 1958, 157.
25. L. N. Markovskii, L. S. Bobkova, V. E. Pasnik, J. Org. Chem. USSR 1981, 17, 1699-1703.
26. D. F. Shellhamer, D. T. Anstine, K. M. Gallego, B. R. Ganesh, A. A. Hanson, K. A. Hanson, R. D. Henderson, J. M. Prince, V. L. Heasley, J. Chem. Soc., Perkin Trans. 2 1995, 861-866.
27. 31P NMR: [17a] M. P. Coogan, M. J. P. Hager, J. Chem. Soc., Perkin Trans. 2 1994, 2101-2107.
28. 13C NMR: [17b] D. J. Collins, P. F. Drygala, J. M. Swan, Aust. J. Chem. 1983, 36, 2517-2536.
29. R. J. Brooks, C. A. Bunton, J. Org. Chem. 1975, 40, 2059-2064.
30. P. J. Weidert, E. Geyer, L. Horner, Phosphorus Sulfur Silicon 1989, 45, 55-59.
31. M. Regitz, A. Liedhegener, W. Anschütz, H. Eckes, Chem. Ber. 1971, 104, 2177-2194.
32. D. J. Burton, D. M. Wiemers, J. Fluorine Chem. 1985, 27, 85-90.
33. [22a] G. M. Blackburn, D. E. Kent, J. Chem. Soc., Chem. Commun. 1981, 511-513.
34. [22b] G. M. Blackburn, D. E. Kent, J. Chem. Soc., Perkin Trans. 1 1986, 913-917.
35. D. B. Berkowitz, M. Bose, T. J. Pfannenstiel, T. Doukov, J. Org. Chem. 2000, 65, 4498-4508.
36. For reasons of brevity, (αR*,βR*) isomers containing no other chiral centers are referred to as l isomers, and the corresponding (αR*,βS*) isomers as u isomers.
37. For example: [25a] C. R. Johnson, J. R. Zeller, Tetrahedron 1984, 40, 1225-1233.
38. [25b] J. T. Negri, L. A. Paquette, J. Am. Chem. Soc. 1992, 114, 8835-8841.
39. [25c] N. Greeves, L. Lyford, J. E. Pease, Tetrahedron Lett. 1994, 35, 285-288.
40. [25d] K. M. Depew, S. J. Danishefsky, N. Rosen, L. Sepp-Lorenzino, J. Am. Chem. Soc. 1996, 118, 12463-12464.
41. For example: [26a] G. Stork, J. M. Stryker, Tetrahedron Lett. 1983, 24, 4887-4890.
42. [26b] B. M. Trost, D. J. Jebaratnam, Tetrahedron Lett. 1987, 28, 1611-1614.
43. [26c] M. D. Preite, M. Gonzalez-Sierra, J. Zinczuk, E. A. Rúveda, Tetrahedron: Asymmetry 1994, 5, 503-506.
44. For example: A. D. Buss, S. Warren, J. Chem. Soc., Perkin Trans. 1 1985, 2307-2325.
45. F. Bergmann, A. Kalmus, E. Breuer, J. Am. Chem. Soc. 1958, 80, 4540-4543.
46. K. Kataoka, S. Tsuboi, Synthesis 2000, 452-456.
47. J. Park, S. F. Pedersen, J. Org. Chem. 1990, 55, 5924-5926.
48. T. Satoh, T. Fujii, K. Yamakawa, Bull Chem. Soc. Jpn. 1990, 63, 1266-1268.
49. N. Radembino, P. M. Loiseau, M.-C. Dessalles, L. Marchat, C. Bories, P. Gayral, G. Mahuzier, Arzneim.-Forsch./Drug Res. 1998, 48 (I), 294-299.
50. W. R. Dolbier, Jr., M. D. Bartberger, J. Org. Chem. 1995, 60, 4984-4985.
51. S. H. Lee, J. Schwartz, J. Am. Chem. Soc. 1986, 108, 2445-2447.
52. V. K. Byistro, L. A. Krichevskii, Z. M. Mildakhmetov, J. Gen. Chem. USSR 1976, 46, 781-782.
53. M. Regitz, W. Anschütz, Chem. Ber. 1969, 102, 2216-2229.
54. E. Elkik, C. Francesch, C. R. Acad. Sci. Paris 1970, 270 C, 443-445.
55. H. Uno, K. Sakamoto, F. Semba, H. Suzuki, Bull. Chem. Soc. Jpn. 1992, 65, 210-217.
56. G. Marchese, F. Naso, Boll. Sci. Fac. Chim. Ind. Bologna 1968, 26, 283-293.
57. M. A. Tius, J. K. Kawakami, Tetrahedron 1995, 51, 3997-4010.
58. M. L. Boys, E. W. Collington, H. Finch, S. Swanson, J. F. Whitehead, Tetrahedron Lett. 1988, 29, 3365-3368.