Catalytic phosphorylation using a bifunctional imidazole derived nucleophilic catalyst

Chemical Communications

Volumn , Issue 30, 2005, Pages 3832-3834

  Jones, Simon ^a   Northen, Julian ^b   Rolfe, Alan ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b Onyx Scientific   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE; POLYETHER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; PHOSPHORYLATION;

EID: 23744499420     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b506344b     Document Type: Article

References (19)

1. (a) R. Wegler, Liebigs Ann. Chem., 1932, 498, 62;
2. (b) W. Steglich and G. Hofle, Angew. Chem., Int. Ed. Engl., 1969, 8, 981;
3. (c) S. K. Chaudhary and O. Hernandez, Tetrahedron Lett., 1979, 20, 99;
4. (d) U. Ragnarsson and L. Grehn, Acc. Chem. Res., 1998, 31, 494.
5. For reviews, see: (a) A. C. Spivey, A. Maddaford and A. J. Redgrave, Org. Prep. Proceed. Int., 2000, 32, 331;
6. (b) D. E. J. E. Robinson and S. D. Bull, Tetrahedron: Asymmetry, 2003, 14, 1407.
7. For examples, see: (a) J. C. Ruble, H. A. Latham and G. C. Fu, J. Am. Chem. Soc., 1997, 119, 1492;
8. (b) B. R. Sculimbrene, A. J. Morgan and S. J. Miller, J. Am. Chem. Soc., 2002, 124, 11653;
9. (c) E. Vedejs, O. Daugulis, L. A. Harper, J. A. MacKay and D. R. Powell, J. Org. Chem., 2003, 68, 5020;
10. (d) A. C. Spivey, T. Fekner, S. E. Spey and H. Adams, J. Org. Chem., 1999, 64, 9430.
11. E. Vedejs and X. Chen, J. Am. Chem. Soc., 1996, 118, 1809.
12. (a) G. T. Copeland and S. J. Miller, J. Am. Chem. Soc., 2001, 123, 6496;
13. (b) B. R. Sculimbrene and S. J. Miller, J. Am. Chem. Soc., 2001, 123, 10125.
14. For an overview see: M. Shibasaki, M. Kanai and K. Funabashi, Chem. Commun., 2002, 1989.
15. M. Pascaly, M. Duda, A. Rompel, B. H. Sift, W. Meyer-Klaucke and B. Krebs, Inorg. Chim. Acta, 1999, 291, 289.
16. (a) S. Jones and D. Selitsianos, Org. Lett., 2002, 4, 3671;
17. (b) S. Jones, D. Selitsianos, K. J. Thompson and S. M. Toms, J. Org. Chem., 2003, 68, 5211.
18. The reported chemical shift for the adduct of N-methylimidazole and an alkyl-aryl chlorophosphate is in the range of δ - 13.38 → - 14.41 ppm. See W. Dabkowski, F. Cramer and K. Michalski, Tetrahedron Lett., 1987, 28, 3561.
19. J. Nilsson, A. Kraszewski and J. Stawinski, J. Chem. Soc., Perkin Trans. 2, 2001, 2263.