Synthesis of 4-oxo-2-alkenylphosphonates via nitrile oxide cycloaddition: γ-Acylation of allylic phosphonates

Journal of Organic Chemistry

Volumn 65, Issue 1, 2000, Pages 256-257

  Lee, Shi Yong ^a   Lee, Bum Sung ^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

NITRILE; PHOSPHONIC ACID DERIVATIVE;

ACYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; NOTE; ORGANIC CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0000362544     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991261y     Document Type: Note

References (23)

1. For reviews, see: (a) Liu, R. S. H.; Asato, A. E. Tetrahedron 1984, 40, 1931. (b) Sporn, M. B.; Roberts, A. B.; Goodman D. S. The retinoids: Biology, Chemistry and Medicine, 2nd ed.; Raven Press: New York, 1994; pp 319-387.
2. For reviews, see: (a) Liu, R. S. H.; Asato, A. E. Tetrahedron 1984, 40, 1931. (b) Sporn, M. B.; Roberts, A. B.; Goodman D. S. The retinoids: Biology, Chemistry and Medicine, 2nd ed.; Raven Press: New York, 1994; pp 319-387.
3. (a) Van den Tempel, P. J.; Huisman, H. O. Tetrahedron 1966, 22, 293.
4. (b) Gedye, R. N.; Westaway, K. C.; Arora, P.; Bisson, R.; Khalil, A. H. Can. J. Chem. 1977, 55, 1218.
5. (c) Liu, R. S. H.; Asato, A. E. Methods Enzymol 1982, 88, 506.
6. Duhamel, L.; Guillemont, J.; Le Gallic, Y.; Ple, G.; Poirier, J.-M.; Ramondenc, Y.; Chabardes, P. Tetrahedron Lett. 1990, 31, 3129.
7. Font, J.; De March, P. Tetrahedron 1981, 37, 2391.
8. (a) Ohler, E.; Kang, H.-S.; Zbiral, E. Chem. Ber. 1988, 121, 299.
9. (b) Ohler, E.; Kang, H.-S.; Zbiral, E. Synthesis 1988, 623.
10. Muller, E. L.; Modro, A. M.; Modro, T. A. Org. Prep. Proced. Int. 1999, 31, 216.
11. For reviews, see: Torssell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: New York, 1988.
12. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339.
13. Arbuzov, B. A. Pure Appl. Chem. 1964, 9, 307.
14. (a) Yuan, C.; Zhang, R.; Yao, J. Chem. Abstr. 1987, 107, 39948t.
15. (b) Phillips, A. M. M. M.; Modro, T. A. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 41.
16. Caramella, P.; Grunanger, P. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 291-392.
17. Jager, V.; Grund, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 50.
18. 1H NMR analysis.
19. (a) Yuan, C.; Chaozhong, L. Heteroat. Chem. 1992, 3, 637.
20. (b) Gerber, K. P.; Modro, T. A.; Muller, E. L.; Phillips, A. M. M. M. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 75, 19.
21. (c) Al-Badri, H.; About-Jaudet, E.; Combret, J.-C.; Collignon, N. Synthesis 1995, 1401.
22. Al-Badri, H.; About-Jaudet, E.; Collignon, N. Tetrahedron Lett. 1995, 36, 393.
23. Camps, J.; Font, J.; De March, P. Tetrahedron 1981, 37, 2493.