Acylation of α-fluorophosphonoacetate derivatives using magnesium chloride-triethylamine

Tetrahedron

Volumn 55, Issue 45, 1999, Pages 12983-12990

  Kim, Dae Young ^a   Lee, Yong Mi ^a   Choi, Young Jae ^a  

^a Soonchunhyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE DERIVATIVE; MAGNESIUM CHLORIDE; PHOSPHONOACETIC ACID; TRIETHYLAMINE;

ACYLATION; ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0033527798     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00807-8     Document Type: Article

References (43)

1. (a) Hudlicky, M.; Pavalath, A. E. Chemistry of Organic Fluorine Compounds II, ACS, Washington DC, 1995.
2. (b) Filler, R.; Kobayashi, Y. Biomedicinal Aspect of Fluorine Chemistry, Kodansha Ltd., Elsevier Biochemical Press, Tokyo, New York, 1982.
3. Bergman, E. D.; Cohen, S.; Shahak, I. J. Chem. Soc. 1959, 3278.
4. Montellano, P. R. O.; Vinson, W. A. J. Org. Chem. 1977,42,2013.
5. Takeuchi, Y.; Ogura, H.; Kanada, A.; Koizumi, T. J. Org. Chem. 1992, 57, 2196.
6. Yemul, S. S.; Kagan, H. B.Tetrahedron Lett. 1980, 21,277.
7. DesMarteau, D. D. ; Gotoh, Y. J. Fluorine Chem. 1992, 58, 71. DesMarteau, D. D. ; Gotoh, Y. J. Chem. Soc. Chem., Commun. 1991, 179. Davis, F. A.; Ran, W.; Murphy, C. K. J. Org. Chem. 1995, 60, 6730.
8. DesMarteau, D. D. ; Gotoh, Y. J. Fluorine Chem. 1992, 58, 71. DesMarteau, D. D. ; Gotoh, Y. J. Chem. Soc. Chem., Commun. 1991, 179. Davis, F. A.; Ran, W.; Murphy, C. K. J. Org. Chem. 1995, 60, 6730.
9. DesMarteau, D. D. ; Gotoh, Y. J. Fluorine Chem. 1992, 58, 71. DesMarteau, D. D. ; Gotoh, Y. J. Chem. Soc. Chem., Commun. 1991, 179. Davis, F. A.; Ran, W.; Murphy, C. K. J. Org. Chem. 1995, 60, 6730.
10. Bank, R. E.; Lawrence, N. J.; and Popplewell, A. L. J. Chem. Soc. Chem. Commun. 1994, 343.
11. McBee, E. T.; Pierce, O. R.; Kilbourne, H. W.; Wilson,E. R. J. Am. Chem. Soc. 1953, 75, 3152.
12. Ishikawa, N.; Takaoka, A.; Iwakiri, H.; Kubota, S.; Kagaruki, S. R. F. Chem. Lett. 1980, 1107. Ishikawa, N.; Takaoka, A.; Ibrahim, K. J. J. Fluorine Chem. 1984, 25, 203.
13. Ishikawa, N.; Takaoka, A.; Iwakiri, H.; Kubota, S.; Kagaruki, S. R. F. Chem. Lett. 1980, 1107. Ishikawa, N.; Takaoka, A.; Ibrahim, K. J. J. Fluorine Chem. 1984, 25, 203.
14. Thenappan, A.; Burton, D. J. Tetrahedron Lett. 1989, 30, 6113. Thenappan, A.; Burton, D. J. J. Org. Chem. 1991, 56, 273.
15. Thenappan, A.; Burton, D. J. Tetrahedron Lett. 1989, 30, 6113. Thenappan, A.; Burton, D. J. J. Org. Chem. 1991, 56, 273.
16. Linderman, R. J.; Graves,D. M. J. Org. Chem. 1989, 54, 661.
17. Coutrot, P.J.; Grison, C. Tetrahedron Lett. 1988, 29, 2655.
18. For general reviews, see: (a) Maryanoff, B. E. ; Beitz, A. B. Chem.Rev. 1989, 89, 863.
19. (b) Wadsworth, W. S. Jr. Org. React.(N. Y.) 1977,25,73.
20. (c) Walker, B. J. Organophosphorus in Organic Synthesis, Cadogan, J. I. G. Ed. Academic Press: New York, 1974, pp 155-206.
21. (d) Kelly, S. E. In Comprehensive Organic Synthesis ; Trost, B. M.; Fleming, I.; Schreiber, S. L. Eds.; Pergamon Press: Oxford, 1991; Vol. 1, Chapter 3.1, pp 755-782.
22. (a) Burton, D. J.; Yang, Z-Y.; Morken, P. A. Tetrahedron 1994, 50, 2993.
23. (b) Lee, S. H.; Schwarte, J. J. Am. Chem. Soc. 1986, 108, 2445.
24. (c) Cox, D. G.; Gurusamy, N.; Burton, D. J. J. Am. Chem. Soc. 1985, 107, 2811.
25. (d) McCarthy, J. R.; Jarvi, E. T.; Matthews, D. P.; Edwards, M. L.; Prakash, N. J.; Bowlin, T. L.; Mehsi, S.; Sunkara, P. S.; Bey, P. J. Am. Chem. Soc. 1989, 111, 1127.
26. (e) Carrell, H. L.; Glusker, J. P.; Burger, V.; Manfre, F.; Trisch, D. ; Biellmann, J. F. Proc.Natl. Acad. Sci USA 1989,56,4440.
27. (a) Allmendinger, T.; Felder, E.; Hungerbuehler, E. In Selective Fluorination in Organic and Bioorganic Chemisty, Welch, J. T. Ed.; ACS symposium series 456, ACS: Washington, DC 1991; p 186.
28. (b) Gross, R. S.; Mehdi, S.; McCarthy, J. R. Tetrahedron Lett. 1993, 34, 7197.
29. (a) Matthews, D. P.; Edwards, M. L.; Mehdi, S.; Koehl, J. R.; Wolos, J. A.; McCarthy, J. R. Bio & Med. Chem. Lett. 1993, 3, 165.
30. (b) Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Chem. Soc., Chem. Commun. 1988,317.
31. Khrimian, A. P.; DeMilo, A. B.; Waters, R. M.; Liquide, N. J.; Nicholson, J. M. J. Org. Chem. 1994, 59, 8034.
32. (a)Blackburn, G. M.; Parratt, M. J. J Chem. Soc., Chem. Commun. 1983, 886.
33. (b) Blackburn, G. M.; Parratt, M. J. J. Chem. Soc. Perkin Trans, 1 1986, 1425.
34. Kim, D. Y.; Kim, J. Y. Synth. Commun. 1998, 28, 2483.
35. For preliminary communication, see: Kim, D. Y.; Rhie, D. Y.; Oh, D. Y. Tetrahedron Lett. 1996, 37, 653.
36. (a) Hong, J. E.; Shin, W. S.; Jang, W. B.; Oh, D. Y. J. Org. Chem. 1996, 61, 2199.
37. (b) Piettre, S. R.; Cirol, C.; Scheicher, C. G. Tetrahedron Lett. 1996, 37, 4711.
38. (c) Durrant, G,; Sutherland, J. K. J. Chem. Soc. Perkin Trans. 1, 1972, 2582.
39. (d) For a review see: Caubere, P.; Coutrot, P. Reduction of P-C bond, in Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Eds.; Pergamon Press: Oxford, 1991; Vol. 8, pp 858-870.
40. Patois, C.; Savignac, P. Synth. Commun. 1994, 24,1317. Elikik, E.; Imbeaux, M. Synthesis 1989, 861.
41. Patois, C.; Savignac, P. Synth. Commun. 1994, 24,1317. Elikik, E.; Imbeaux, M. Synthesis 1989, 861.
42. Coutrot, Ph.; Grison, C.; Sauvetre, R. J. Organomet. Chem. 1987, 332, 1.
43. Bridge, C. F.; O'Hagan, D. J. Fluorine Chem. 1997, 82, 21.