Dephosphonylation of β-carbonyl phosphonates

Journal of Organic Chemistry

Volumn 64, Issue 19, 1999, Pages 7017-7022

  Lee, Shi Yong ^a   Lee, Chi Wan ^a   Oh, Dong Young ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBONYL DERIVATIVE; KETONE DERIVATIVE; LITHIUM DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; DEPHOSPHORYLATION; REACTION ANALYSIS;

EID: 0344117769     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990221r     Document Type: Article

References (34)

1. Krapcho, A. P. Synthesis 1982, 893.
2. (a) Kinoshita, H.; Hori, I.; Oishi, T.; Ban, Y. Chem. Lett. 1984, 1517.
3. (b) Kurth, M. J.; O'Brien, M. J. J. Org. Chem. 1985, 50, 3846.
4. (c) Fujii, M.; Nakamura, K.; Mekata, H.; Oka, S.; Ohno, A. Bull. Chem. Soc. Jpn. 1988, 61, 495.
5. To distinguish between "dephosphorylation" and "dephosphonylation", we use the term "dephosphonylation" as a limited meaning of P-C bond cleavage in a compound bearing phosphonate groups.
6. (a) Bestmann, H. J.; Schultz, H. Chem. Ber. 1962, 95, 2921.
7. (b) Okamoto, Y.; Iwamato, N.; Takamuku, S. J. Chem. Soc., Chem. Commun. 1986, 1516.
8. (c) Bestmann, H. J.; Graf, G.; Kolewa, S.; Vilsmeier, E. Chem. Ber. 1970, 103, 2974.
9. (d) Kondo, K.; Negishi, A.; Tunemoto, D. Angew. Chem., Int. Ed. Engl. 1974, 13, 407.
10. We reported that enamine phosphonates bearing α-stabilized groups such as phenyl or thiophenyl gave the corresponding deoxybenzoin or β-keto sulfides during basic hydrolysis. Lee, K.; Oh, D. Y. Bull. Kor. Chem. Soc. 1991, 12, 254.
11. 3AlH among them cleaved the P-C bond selectively to give the corresponding β-keto ester. However, the mechanism and any application of the dephosphonylation were not reported. Durrant, G.; Sutherland, J. K. J. Chem. Soc., Perkin Trans. 1 1972, 2582.
12. Hong, J. E.; Shin, W. S.; Jang, W. B.; Oh, D. Y. J. Org. Chem. 1996, 61, 2199.
13. Jang, W. B.; Shin, W. S.; Hong, J. E.; Lee, S. Y.; Oh, D. Y. Synth. Commun. 1997, 27, 3333.
14. Some of our results described herein have been preliminarily presented in a short communication. Lee, S. Y.; Hong, J. E.; Jang, W. B.; Oh, D. Y. Tetrahedron Lett. 1987, 38, 4567.
15. (a) Savignac, P.; Mathey, F. Tetrahedron Lett. 1976, 2829.
16. (b) Calogeropoulou, T.; Hammond, G. B.; Wiemer, D. F. J. Org. Chem. 1987, 52, 2, 4185.
17. (c) Grieco, P. A.; Pogonowski, C. S. J. Am. Chem. Soc. 1973, 95, 3071.
18. (a) Clark, R. D.; Kozar, L. G.; Heathcock, C. H. Synthesis 1975, 635.
19. (b) Ruder, S. M.; Kulkarni, V. R. Synthesis 1998, 945.
20. Kem, K. M.; Nguyen, N. V.; Cross, D. J. J. Org. Chem. 1981, 46, 5188.
21. Tay, M. K.; About-Jaudet, E.; Collignon, N.; Savignac, P. Tetrahedron 1989, 45, 4415.
22. (a) Lebel, N. A.; Cherluck, R. M.; Curtis, E. A. Synthesis 1973, 678.
23. (b) Schoenberg, A.; Heck, R. F. J. Org. Chem. 1974, 39, 3327.
24. (c) Mattingly, P. G.; Miller, M. J. J. Org. Chem. 1980, 45, 410.
25. (d) Pfister, J. R.; Wymann, W. E. Synthesis 1983, 38.
26. (e) Zaloom, J.; Calandra, M.; Roberts, D. C. J. Org. Chem. 1985, 50, 2601.
27. (f) Blagbrough, I. S.; Mackenzie, N. E.; Ortiz, C.; Scott, A. I. Tetrahedron Lett. 1988, 27, 1251.
28. Balczewski, P.; Pietrzykowski, W. M.; Mikolajczyk, M. Tetrahedron 1995, 51, 7727.
29. Araujo, H. C.; Mahajan, J. R. Synthesis 1978, 228.
30. Shibata, I.; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett. 1993, 1953.
31. (a) Koziara, A.; Zawadzki, S.; Zwierzak, A. Synthesis 1979, 527.
32. (b) Kita, Y.; Akai, S.; Ajimura, N.; Yoshigi, M.; Tsugoshi, T.; Yasuda, H.; Tamura, Y. J. Org. Chem. 1986, 51, 4150.
33. Zhang, Z.; Scheffold, R. Helv. Chim. Acta 1993, 76, 2602.
34. Roblot, G.; Wylde, R.; Martin, A.; Parello, J. Tetrahedron 1993, 49, 6381.