Facile enolisation of α-ketophosphonates

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1663-1666

  Afarinkia, Kamyar ^a   Echenique, Juan ^a   Nyburg, Stanley C ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; X RAY ANALYSIS;

EID: 0031550863     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00157-3     Document Type: Article

References (18)

1. 1. Afarinkia K.; Vinader, M. V. "The Synthesis of Acyl Phophorus, -Arsenic, -Antimony or -Bismuth Functions". In Organic Functional Group Transformations Moody, C. J. Ed.; Elsevier: London, 1995; pp 393-407.
2. 2. a) Imine: Karaman, R.; Goldblum, A.; Breuer E.; Leader, H. J. Chem. Soc., Perkin Trans. 1 1989, 765.
3. b) Hydrazone: Scherer, H.; Hartmann, A.; Regitz, M.; Tunggal, B. D.; Günther, H. Chem. Ber. 1972, 105, 3357.
4. c) Oxime: Breuer, E.; Zaher, H.; Tashma, Z. Tetrahedron Lett., 1992, 33, 2067.
5. 3. Oshikawa, T.; Yamashita, M. Bull. Chem. Soc. Jpn. 1990, 63, 2728. Karaman, R.; Goldblum, A.; Breuer, E.; Leader, H. J. Chem. Soc., Perkin Trans. 1 1989, 765. See also ref 2a.
6. 3. Oshikawa, T.; Yamashita, M. Bull. Chem. Soc. Jpn. 1990, 63, 2728. Karaman, R.; Goldblum, A.; Breuer, E.; Leader, H. J. Chem. Soc., Perkin Trans. 1 1989, 765. See also ref 2a.
7. 4. Yamashita, M.; Kojima, M.; Yoshida, H.; Ogata, T.; Inokawa, S. Bull. Chem. Soc. Jpn. 1980, 53, 1625.
8. 5. Breuer, E.; Karaman, R.; Goldblum A.; Leader, H. J. Chem. Soc., Perkin Trans. 2 1988, 2029. Fuji, M.; Ozaki, K.; Sekine, M.; Hata, T. Tetrahedron 1987, 43, 3395. Kume, A.; Fujii, M.; Sekine, M.; Hata, T. J. Org. Chem. 1984, 49, 2139; Sekine, M.; Satoh, M.; Yamagata, H.; Hata, T. J. Org. Chem. 1980, 45, 4162. See also ref 2a.
9. 5. Breuer, E.; Karaman, R.; Goldblum A.; Leader, H. J. Chem. Soc., Perkin Trans. 2 1988, 2029. Fuji, M.; Ozaki, K.; Sekine, M.; Hata, T. Tetrahedron 1987, 43, 3395. Kume, A.; Fujii, M.; Sekine, M.; Hata, T. J. Org. Chem. 1984, 49, 2139; Sekine, M.; Satoh, M.; Yamagata, H.; Hata, T. J. Org. Chem. 1980, 45, 4162. See also ref 2a.
10. 5. Breuer, E.; Karaman, R.; Goldblum A.; Leader, H. J. Chem. Soc., Perkin Trans. 2 1988, 2029. Fuji, M.; Ozaki, K.; Sekine, M.; Hata, T. Tetrahedron 1987, 43, 3395. Kume, A.; Fujii, M.; Sekine, M.; Hata, T. J. Org. Chem. 1984, 49, 2139; Sekine, M.; Satoh, M.; Yamagata, H.; Hata, T. J. Org. Chem. 1980, 45, 4162. See also ref 2a.
11. 5. Breuer, E.; Karaman, R.; Goldblum A.; Leader, H. J. Chem. Soc., Perkin Trans. 2 1988, 2029. Fuji, M.; Ozaki, K.; Sekine, M.; Hata, T. Tetrahedron 1987, 43, 3395. Kume, A.; Fujii, M.; Sekine, M.; Hata, T. J. Org. Chem. 1984, 49, 2139; Sekine, M.; Satoh, M.; Yamagata, H.; Hata, T. J. Org. Chem. 1980, 45, 4162. See also ref 2a.
12. 6. Tam, C. C.; Mattocks, K. L.; Tishler, M. Proc. Natl. Acad. Sci. USA 1981, 78, 3301; Longmire, C. F.; Evans Jr. S. L. J. Chem. Soc. Chem. Commun. 1990, 922.
13. 6. Tam, C. C.; Mattocks, K. L.; Tishler, M. Proc. Natl. Acad. Sci. USA 1981, 78, 3301; Longmire, C. F.; Evans Jr. S. L. J. Chem. Soc. Chem. Commun. 1990, 922.
14. 7. All new compounds were fully characterized (ir, nmr, ms) and high resolution mass spectrometry was used to confirm the composition of their molecular ions. NMR data were obtained on a Bruker AM360 MHz NMR. Mass spectra were obtained on a Jeol AX505W mass spectrometer using electron impact (EI), chemical ionisation (CI) or fast atom bombardment (FAB) techniques.
15. 8. Cassidei, L.; Dell'Atti, A.; Sciacovelli, O. Z. Naturforsch C (Biological Sci) 1976, 31C, 641.
16. -3. Bond C7-C8 is 1.34(3) Å long and hence is a double bond, confirming O1 to be an enol, not keto, oxygen. Pairs of molecules related by centers of symmetry are O1-H....O3 hydrogen bonded with the O...O distance of 2.61(2) Å. Full crystallographic details are deposited in the Cambridge Organic Crystal database.
17. 5 (MH+) 209.0579, found 209.0557.
18. 11. Sekine, M.; Kume, A.; Nakajima, M.; Hata, T. Chem. Letters 1981, 1087 and references cited therein.