Stereoselective synthesis of α-monofluorinated phosphonate mimetics of naturally occurring phosphoserine and phosphothreonine, via electrophilic fluorination of lithiated bis-lactim ethers

Chemical Communications

Volumn 2, Issue 15, 2002, Pages 1600-1601

  Ruiz, María ^a   Ojea, Vicente ^a   Quintela, José M ^a   Guillín, Juan J ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 4 PHOSPHONOBUTYRIC ACID; ETHER; LACTAM; NATURAL PRODUCT; PEPTIDE; PHOSPHONIC ACID DERIVATIVE; PHOSPHOSERINE; PHOSPHOTHREONINE; VALINE;

ARTICLE; CHEMICAL REACTION; ENANTIOMER; FLUORINATION; LITHIATION; PROTECTION; PROTEIN SYNTHESIS; SOLID;

EID: 0036073387     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/b204093j     Document Type: Article

References (16)

1. M. D. Jackson, J. M. Denu, Chem. Rev. 2001 101 2313
2. A. McCluskey, A. T. R. Sim, J. A. Sakoff, J. Med. Chem. 2002 45 1151
3. G. M. Blackburn, D. Brown, S. J. Martin, M. J. Parratt, J. Chem. Soc., Perkin Trans. 1 1987 181
4. D. O’Hagan, H. S. Rzepa, Chem. Commun. 1997 645
5. D. B. Berkowitz, M. B. Bose, T. J. Pfannenstiel, T. Doukov, J. Org. Chem. 2000 65 4498
6. J. Nieschalk, A. S. Batsanov, D. O’Hagan, J. A. K. Howard, Tetrahedron 1996 52 165
7. T. R. Burke, M. S. Smyth, A. Otaka, M. Nomizu, P. R. Roller, G. Wolf, R. Case, S. E. Shoelson, Biochemistry 1994 33 6490
8. A. Otaka, E. Mitsuyama, T. Kinoshita, H. Tamamura, N. Fujii, J. Org. Chem. 2000 65 4888
9. B. Berkowitz, D. B. M. J. Eggen, Q. Shen, R. K. Shoemaker, J. Org. Chem. 1996 61 4666
10. A. Otaka, E. Mitsuyama, H. Watanabe, H. Tamamura, N. Fujii, Chem. Commun. 2000 1081
11. V. Ojea, M. Ruiz, G. Shapiro, E. Pombo-Villar, J. Org. Chem. 2000 65 1984
12. M. Ruiz, V. Ojea, G. Shapiro, H.-P. Weber, E. Pombo-Villar, Tetrahedron Lett. 1994 35 4551
13. G. Shapiro, D. Buechler, V. Ojea, E. Pombo-Villar, M. Ruiz, H.-P. Weber, Tetrahedron Lett. 1993 34 6255
14. M. C. Fernández, J. M. Quintela, M. Ruiz, V. Ojea, Tetrahedron: Asymmetry 2002 13 233
15. S. D. Taylor, C. C. Kotoris, G. Hum, Tetrahedron 1999 55 12431
16. E. Differding, R. O. Duthaler, A. Krieger, G. M. Rüegg, C. Schmit, Synlett 1991 395