Chiral, non-racemic α-hydroxyphosphonates and phosphonic acids via stereoselective hydroxylation of diallyl benzylphosphonates

Tetrahedron Asymmetry

Volumn 14, Issue 2, 2003, Pages 265-273

  Skropeta, Danielle ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

MANDELIC ACID DERIVATIVE; OXAZIRIDINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARBUZOV REACTION; ARTICLE; CHIRALITY; DEPROTECTION REACTION; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; HYDROXYLATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0037449605     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00786-3     Document Type: Article

References (38)

1. Pompliano D.L., Rands E., Schaber M.D., Mosser S.D., Anthony N.J., Gibbs J.B. Biochemistry. 31:1992;3800-3807.
2. Sikorski J.A., Miller M.J., Braccolino D.S., Cleary D.G., Corey S.D., Font J.L., Gruys K.J., Han C.Y., Lin K.-C., Pansegrau P.D., Ream J.E., Schnur D., Shah A., Walker M.C. Phosphorus Sulfur Silicon. 76:1993;115-118.
3. Burke T.R., Li Z.-H., Bolen J.B., Marquez V.E. J. Med. Chem. 34:1991;1577-1581.
4. Stowasser B., Budt K.-H., Jian-Qi L., Peyman A., Ruppert D. Tetrahedron Lett. 33:1992;6625-6628.
5. Patel D.V., Rielly-Gauvin K., Ryono D.E., Free C.A., Rogers W.L., Smith S.A., Oehl R.S., Petrillo E.W. Jr. J. Med. Chem. 38:1995;4557-4569.
6. Mueller B., Schaub C., Schmidt R.R. Angew. Chem., Int. Ed. 37:1998;2893-2897.
7. Wiemer D.F. Tetrahedron. 53:1997;16609-16644.
8. Groeger H., Hammer B. Chem. Eur. J. 6:2000;943-948.
9. Rowe B.J., Spilling C.D. Tetrahedron: Asymmetry. 12:2001;1701-1708.
10. Yokomatsu T., Yamagishi T., Shibuya S. Tetrahedron: Asymmetry. 4:1993;1401-1404.
11. Cermak D.M., Yanming D., Wiemer D.F. J. Org. Chem. 64:1999;388-393.
12. Hammerschmidt F., Linder W., Wuggenig F., Zarbl E. Tetrahedron: Asymmetry. 11:2000;2955-2964.
13. Blazis V.J., Koeller K.J., Spilling C.D. J. Org. Chem. 60:1995;931-940.
14. 10 write ".hydrolysis of the phosphonamides by reaction with 4 M HCl in dioxane only resulted in decomposition".
15. Dickson J.K. Jr., Biller S.A., Magnin D.R., Petrillo E.W. Jr., Hillyer J.W., Hsieh D.C., Lan S.-J., Rinehart J.K., Gregg P.E., Harrity T.W., Julibuis K.G., Kalinowski S.S., Kinselman L.K., Mookhtiar K.A., Ciosek C.P. Jr. J. Med. Chem. 39:1996;661-664.
16. Kamber M., Just G. Can. J. Chem. 63:1985;823-827.
17. Schaub C., Mueller B., Schmidt R.R. Eur. J. Org. Chem. 9:2000;1745-1758.
18. Ruiz M., Ojea V., Shapiro G., Weber H.-P., Pombo-Villar E. Tetrahedron Lett. 35:1994;4551-4554.
19. Berkowitz D.B., Sloss D.G. J. Org. Chem. 60:1995;7047-7050.
20. Pogatchnik D.M., Wiemer D.F. Tetrahedron Lett. 38:1997;3495-3498.
21. Kunz H., Unverzagt C. Angew. Chem., Int. Ed. Engl. 23:1984;36.
22. Schwoerer R., Schmidt R.R. J. Am. Chem. Soc. 124:2002;1632-1637.
23. Bhattacharya A.K., Thyagarajan G. Chem. Rev. 81:1981;415-430.
24. Kozlowski J.K., Rath N.P., Spilling C.D. Tetrahedron. 51:1995;6385-6396.
25. Zwierak A., Kluba M. Tetrahedron. 27:1971;3163-3170.
26. Other phosphonic acid esterification methods such as heating the free phosphonic acids in triethylorthoformate (Gilmore, W. F.; McBride, H. A. J. Pharm. Sci. 1974, 63, 1087-1090) or refluxing benzene containing O-diakyl N,N′-dicyclohexylurea (Elhaddadi, M.; Jacquier, R.; Gastal, F.; Petrus, C.; Petrus, F. Phosphorus Sulfur Silicon 1990, 54, 143-150) gave poor yields of diethyl phosphonates with low specific rotation values, indicative of racemisation.
27. Smaardijk A.A., Noorda S., van Bolhuis F., Wynberg H. Tetrahedron Lett. 26:1985;493-496.
28. Jork H., Funk W., Fischer W., Wimmer H. Thin-Layer Chromatography. Reagents and Detection Methods. 1a:1990;VCH, Weinheim.
29. Still W.C., Kahn M., Mitra A. J. Org. Chem. 43:1978;2923-2925.
30. Shapiro E.A., Eismont M. Yu., Pereverzeva Yu. O., Nefedov A.O., Strashnenko A.V., Kostyrko I.N., Roslavtseva S.A. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.). 39:1990;573-577.
31. Detert, H.; Sugiono, E. J. Phys. Org. Chem. 2000, 587-590. NMR spectral data were not reported.
32. Toy, A. D. F.; Cooper, R. S. J. Am. Chem. Soc. 1954, 76, 2191-2195. NMR spectral data were not reported.
33. Hammerschmidt F., Hanninger A. Chem. Ber. 128:1995;823-830.
34. Kormachev V.V., Kolyamshin O.A., Mitrasov Yu. N., Anisimova E.A. J. Gen. Chem. USSR. 1992;478-482.
35. Creary, X.; Underiner, T. L. J. Org. Chem. 1985, 50, 2165-2170. NMR spectral data were not reported.
36. Albouy D., Brun A., Munoz A., Etemad-Moghadam G. J. Org. Chem. 63:1998;7223-7230.
37. St. Maurice M., Bearne S.L. Biochemistry. 39:2000;13324-13335.
38. Gibbs, J. B.; Koblan, K. S.; Macleod, A. M.; Merchant, K. J. Int. Pat. Appl. US 5,519,163, 1995.