Facile dephosphonylation of β-ketophosphonic acids: Mechanistic studies

Organic Letters

Volumn 8, Issue 16, 2006, Pages 3429-3431

  Hawkins, Michael J ^a   Powell, Eugene T ^a   Leo, Gregory C ^a   Gauthier, Diane A ^a   Greco, Michael N ^a   Maryanoff, Bruce ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

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EID: 33747301812     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060519l     Document Type: Article

References (17)

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4. Hwang, J.; Choi, J. Drugs Future 2004, 29, 163.
5. (a) de Garavilla, L.; Greco, M. N.; Sukumar, N.; Chen, Z.; Pineda, A. O.; Mathews, F. S.; Di Cera, E.; Giardino, E. C.; Wells, G. I.; Haertlein, B. J.; Kaufman, J. A.; Corcoran, T. J.; Derian, C. K.; Eckardt, A. J.; Damiano, B. P.; Andrade-Gordon, P.; Maryanoff, B. E. J. Biol. Chem. 2005, 280, 18001.
6. (b) Greco, M. N.; Hawkins, M. J.; Powell, E. T.; Almond, H. R., Jr.; Corcoran, T. W.; de Garavilla, L.; Kauffman, J. A.; Recacha, R.; Chattopadhyay, D.; Andrade-Gordon, P.; Maryanoff, B. E. J. Am. Chem. Soc. 2002, 124, 3810.
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8. For an isolated case, see: Denmark, S. E.; Marlin, J. E. J. Org. Chem. 1991, 56, 1003.
9. (a) Piettre, S. G.; Girol, C.; Schelcher, C. G. Tetrahedron Lett. 1996, 37, 4711.
10. (b) Thenappan, A.; Burton, D. J. J. Org. Chem. 1991, 56, 273.
11. (c) Thenappan, A.; Burton, D. J. Tetrahedron Lett. 1989, 30, 6113.
12. (d) Thenappan, A.; Burton, D. J. Tetrahedron Lett. 1989, 30, 3641.
13. (e) Among the possibilities in Table 1, Horner-Emmons elimination is least likely because related substrates have been shown to be thermally stable. See: Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763.
14. On exposure of the corresponding diethyl phosphonate of 3 to the conditions of Table 1 for up to 2 h, no dephosphonylation was observed.
15. Westheimer, F. H. Chem. Rev. 1981, 81, 313.
16. 31P NMR over 2.5 h.
17. The free phosphonic acid was used at each pH. Rates were compared at 10 min because the product mixture became complex at pH 10 after 10 min.