Efficient one-pot synthesis of β-hydroxyphosphonates: regioselective nucleophilic ring opening reaction of epoxides with triethyl phosphite catalyzed by Al(OTf)3

Tetrahedron

Volumn 65, Issue 36, 2009, Pages 7691-7695

  Sobhani, Sara ^a   Vafaee, Asieh ^a  

^a UNIVERSITY OF BIRJAND   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM DERIVATIVE; EPOXIDE; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; ONE POT SYNTHESIS; PRIORITY JOURNAL; RING OPENING;

EID: 67949119014     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.106     Document Type: Article

References (50)

1. Emsle J., and Hall E.D. The Chemistry of Phosphorus (1976), Harper and Row, London
2. Lejczak B., Kafarski P., Sztajer H., and Mastalerz P. J. Med. Chem. 29 (1986) 2212-2217
3. Engle R. Chem. Rev. 77 (1977) 349-367
4. Takahashi E., Kimura T., Nakamura K., Arahira M., and Iida M. J. Antibiot. 48 (1995) 1124-1129
5. Kafarski P., and Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem. 63 (1991) 193-215
6. Allen M.C., Fuher W., Tuck R., and WadeWood J.M. J. Med. Chem. 32 (1989) 1652-1661
7. Fields S.C. Tetrahedron 55 (1999) 12237-12273
8. Truel I., Mohamed-Hachi A., About-Jaudet E., and Collignon N. Synth. Commun. 27 (1997) 297-302
9. Chengfu X., and Chengye Y. Eur. J. Org. Chem. (2004) 4410-4415
10. Lambert J.B., Emblidge R.W., and Zhao Y. J. Org. Chem. 59 (1994) 5397-5403
11. Zurawinski R., Nakamura K., Drabowicz J., Kielbasinski P., and Mikolajczyk M. Tetrahedron: Asymmetry 12 (2001) 3139-3145
12. Yong-Hui Z., and Chengfu X. Chin. J. Chem. 21 (2003) 883-892
13. Madec J., Pfitser X., Phanasavath P., and Ratovelomanana-Vidal V. Tetrahedron 57 (2001) 2563-2568
14. Gautier I., Ratovelomanana-Vidal V., Savignac P., and Genet J.P. Tetrahedron Lett. 37 (1996) 7721-7724
15. Kitamura M., Tokunaga M., and Noyori R. J. Am. Chem. Soc. 117 (1995) 2931-2932
16. Zymanczyk-Duda E., Lejczak B., and Kafarski P. Tetrahedron 51 (1995) 11804-11809
17. Duparte de paul S., Jeulin S., Ratovelomanana-Vidal V., Genet J.P., Champion N., and Dellis P. Eur. J. Org. Chem. (2003) 1931-1941
18. Duparte de paul S., Jeulin S., Ratovelomanana-Vidal V., Genet J.P., Champion N., Deschaux G., and Dellis P. Org. Process Res. Dev. 7 (2003) 399-406
19. Basckes N., and Sen A. Polyhedron 14 (1995) 197-202
20. Yong-Hui Z., Zuyi L., and Chenegye Y. Tetrahedron Lett. 43 (2002) 3247-3249
21. Lentsch L.M., and Wiemer D.F. J. Org. Chem. 64 (1999) 5205-5212
22. Orsini F., and Lucci E.M. Tetrahedron Lett. 46 (2005) 1909-1911
23. Orsini F. Tetrahedron Lett. 39 (1998) 1425-1428
24. Orsini F., and Caselli A. Tetrahedron Lett. 43 (2002) 7255-7257
25. Arbuzov B.A. Pure Appl. Chem. 9 (1964) 307-336
26. Baboulene M., and Sturtz G. Phosphorus, Sulfur Silicon Relat. Elem. 7 (1979) 101-107
27. Chelintsev G.V., and Kuskov V.K. J. Gen. Chem. USSR 16 (1946) 1481-1484
28. Li Z., Racha S., Dan L., El-Subbagh H., and Abushanab E. J. Org. Chem. 58 (1993) 5779-5783
29. Racha S., Li Z., El-Subbagh H., and Abushanab E. Tetrahedron Lett. 33 (1992) 5491-5494
30. Sardarian A.R., and Shahsavari-Fard Z. Synth. Commun. 37 (2007) 289-295
31. Azizi N., and Saidi M.R. Tetrahedron Lett. 44 (2003) 7933-7935
32. Azizi N., and Saidi M.R. Tetrahedron Lett. 47 (2005) 4515
33. Wadsworth W.S., and Emmons W.D. J. Am. Chem. Soc. 83 (1961) 1733-1738
34. Firouzabadi H., Iranpoor N., Sobhani S., and Amoozgar Z. Synthesis (2004) 1771-1774
35. Firouzabadi H., Iranpoor N., and Sobhani S. Tetrahedron Lett. 43 (2002) 477-480
36. Firouzabadi H., Iranpoor N., and Sobhani S. Tetrahedron 60 (2004) 203-210
37. Sobhani S., Safaei E., Asadi M., Jalili F., and Tashrifi Z. J. Porphyrins Phthalocyanines 12 (2008) 849-856
38. Sobhani S., Safaei E., Asadi M., and Jalili F. J. Orgmet. Chem. 693 (2008) 3313-3318
39. Sobhani S., and Vafaee A. Synthesis (2009) 1909-1915
40. Firouzabadi H., Iranpoor N., and Sobhani S. Synthesis (2004) 2692-2696
41. Firouzabadi H., Iranpoor N., Sobhani S., Ghassemipour S., and Amoozgar Z. Tetrahedron Lett. 44 (2003) 891-893
42. Firouzabadi H., Iranpoor N., Sobhani S., and Ghassamipour S. J. Orgmet. Chem. 689 (2004) 3197-3202
43. Firouzabadi H., Iranpoor N., Sobhani S., and Amoozgar Z. Synthesis (2004) 295-297
44. Sobhani S., and Tashrifi Z. Synth. Commun. 39 (2009) 120-131
45. Sobhani S., and Tashrifi Z. Heteroat. Chem. 20 (2009) 109-115
46. Williams D.B.G., and Lawton M. Tetrahedron Lett. 47 (2006) 6557-6560
47. Williams D.B.G., and Lawton M. Org. Biomol. Chem. 3 (2005) 3269-3272
48. Fringuelli F., Pizzo F., Tortoioli S., and Vaccaro L. J. Org. Chem. 69 (2004) 7745-7747
49. Petrova J., and Kirilov M. Phosphorus, Sulfur Silicon Relat. Elem. 85 (1993) 49-58
50. Wroblewski A.E., and Halajewska-Wosik A. Eur. J. Org. Chem. (2002) 2758-2763