Studies on highly regio- and stereoselective fluorohydroxylation reaction of 3-aryl-1,2-allenyl phosphine oxides with Selectfluor

Tetrahedron

Volumn 65, Issue 38, 2009, Pages 8035-8042

  He, Guangke ^a   Fu, Chunling ^a   Ma, Shengming ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ALLENE DERIVATIVE; PHOSPHINE OXIDE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; HYDROXYLATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 68549120856     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.07.009     Document Type: Article

References (44)

1. O'Hagan D. Chem. Soc. Rev. 37 (2008) 308
2. Smart B.E. J. Fluorine Chem. 109 (2001) 3
3. Zhao C.Q., Han L.B., and Tanaka M. Organometallics 19 (2000) 4196
4. Zapata A.J., Gu Y., and Hammond G.B. J. Org. Chem. 65 (2000) 227
5. Tang W., and Zhang X. Chem. Rev. 103 (2003) 3029
6. Rubin M., Markov J., Chuprakov S., Wink D.J., and Gevorgyan V. J. Org. Chem. 68 (2003) 6251
7. Nishimura T., Hirabayashi S., Yasuhara Y., and Hayashi T. J. Am. Chem. Soc. 128 (2006) 2556
8. Ma S., Guo H., and Yu F. J. Org. Chem. 71 (2006) 6634
9. Chakravarty M., and Kumara Swamy K.C. J. Org. Chem. 71 (2006) 9128
10. For some of the most recent reports on the monofluorination, see:
11. Pacheco M.C., and Gouverneur V. Org. Lett. 7 (2005) 1267
12. Carroll L., Pacheco M.C., Garcia L., and Gouverneur V. Chem. Commun. (2006) 4113
13. Shibatomi K., and Yamamoto H. Angew. Chem., Int. Ed. 47 (2008) 5796
14. Takeuchi Y., Tarui T., and Shibata N. Org. Lett. 2 (2000) 639
15. Nie J., Zhu H., Cui H., Hua M., and Ma J. Org. Lett. 9 (2007) 3053
16. Stavber G., Zupan M., Jereb M., and Stavber S. Org. Lett. 6 (2004) 4973
17. Gustafsson T., Gilmour R., and Seeberger P.H. Chem. Commun. (2008) 3022
18. Zhou C., Ma Z., Gu Z., Fu C., and Ma S. J. Org. Chem. 73 (2008) 772
19. Zhou C., Li J., Lu B., Fu C., and Ma S. Org. Lett. 10 (2008) 581
20. Santelli-Rouvier C., Toupet L., and Santelli M. J. Org. Chem. 62 (1997) 9039
21. Barton D.H.R., Godinho L.S., Hesse R.H., and Pechet M.M. J. Chem. Soc., Chem. Commun. (1968) 804
22. Schack C.J., and Christe K.O. Inorg. Chem. 18 (1979) 2619
23. Tius M.A. Tetrahedron 51 (1995) 6605
24. Schmutzler R. Angew. Chem., Int. Ed. Engl. 7 (1968) 440
25. Rozen S. Chem. Rev. 96 (1996) 1717
26. Umemoto T., Kawada K., and Tomita K. Tetrahedron Lett. 27 (1986) 4465
27. Umemoto T., Fukami S., Tomizawa G., Harasawa K., Kawada K., and Tomita K. J. Am. Chem. Soc. 112 (1990) 8563
28. Resnati G., and DesMarteau D.D. J. Org. Chem. 56 (1991) 4925
29. Banks, R. E. (Air Products and Chemicals, Inc., U.S.A.). U.S. Patent 5,086,178, 1992;
30. Banks R.E., Lawrence N.J., and Popplewell A.L. Synlett (1994) 831
31. Banks R.E., Besheesh M.K., Mohialdin-Khaffaf S.N., and Sharif I. J. Chem. Soc., Perkin Trans. 1 (1996) 2069
32. Nyffeler P.T., Durón S.G., Burkart M.D., Vincent S.P., and Wong C.-H. Angew. Chem., Int. Ed. 44 (2005) 192
33. Singh R.P., and Shreeve J.M. Acc. Chem. Res. 37 (2004) 31
34. Stavber S., and Zupan M. J. Chem. Soc., Chem. Commun. (1994) 149
35. Ma S., Wei Q., and Wang H. Org. Lett. 2 (2000) 3893
36. Ma S., Ren H., and Wei Q. J. Am. Chem. Soc. 125 (2003) 4817
37. Li J., Fu C., Chen G., Chai G., and Ma S. Adv. Synth. Catal. 350 (2008) 1376
38. Fu C., and Ma S. Eur. J. Org. Chem. (2005) 3942
39. He G., Zhou C., Fu C., and Ma S. Tetrahedron 63 (2007) 3800
40. Chen G., Fu C., and Ma S. Tetrahedron 62 (2006) 4444
41. int=0.0219), number of observations [>2σ(I)] 2990, parameters: 226. The Cambridge database file is CCDC-707615.
42. int=0.0290), number of observations [>2σ(I)] 2798, parameters: 241. The Cambridge database file is CCDC-707616.
43. Guo H., Qian R., Guo Y., and Ma S. J. Org. Chem. 73 (2008) 7934
44. He G., Guo H., Qian R., Guo Y., Fu C., and Ma S. Tetrahedron 65 (2009) 4877