Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids

Chemical Communications

Volumn , Issue 10, 2005, Pages 1324-1326

  Bernardi, Luca ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA FLUORO BETA KETO PHOSPHONATE DERIVATIVE; LEWIS ACID; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CHLORINATION; ENANTIOSELECTIVITY; FLUORINATION; OPTICS; PRODUCT RECOVERY; STRUCTURE ANALYSIS;

EID: 16244370763     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b415568h     Document Type: Article

References (39)

1. See e.g.: (a) H. Ibrahim and A. Togni, Chem. Commun., 2004, 1147;
2. (b) K. Muñiz, Angew. Chem. Int. Ed., 2001, 40, 1653;
3. (c) G. Thomas, Medicinal Chemistry: An Introduction, Wiley, New York, 2000.
4. (a) L. Hintermann and A. Togni, Angew. Chem. Int. Ed., 2000, 39, 4359;
5. (b) L. Hintermann, D. Broggini and A. Togni, Helv. Chim. Acta, 2002, 85, 1597;
6. (c) R. Frantz, L. Hintermann, M. Perseghini, D. Broggini and A. Togni, Org. Lett., 2003, 5, 1709;
7. (d) Y. Hamashima, D. Hotta and M. Sodeoka, J. Am. Chem. Soc., 2002, 124, 11240;
8. (e) Y. Hamashima, H. Takono, D. Hotta and M. Sodeoka, Org. Lett., 2003, 5, 3225;
9. (f) D. Y. Kim and E. J. Park, Org. Lett., 2003, 5, 1709;
10. (g) J.-A. Ma and D. Cahard, Tetrahedron: Asymmetry, 2004, 15, 1007;
11. (h) J.-A. Ma and D. Cahard, J. Fluorine Chem., 2004, 125, 1357;
12. (i) N. Shibata, T. Ishimaru, T. Nogai, J. Kohno and T. Toru, Synlett, 2004, 1703.
13. (a) L. Hintermann and A. Togni, Helv. Chim. Acta, 2000, 83, 2425;
14. (b) M. Marigo, N. Kumaraguruburan and K. A. Jørgensen, Chem. Eur. J., 2004, 10, 2133;
15. (c) H. Ibrahim, F. Kleinbeck and A. Togni, Helv. Chim. Acta, 2004, 87, 605;
16. (d) see also: Y. Zhang, S. Shibatomi and H. Yamamoto, J. Am. Chem. Soc., 2004, 126, 15308.
17. (a) H. Wack, A. E. Taggi, A. M. Hafez, W. J. Dury, III and T. Lectka, J. Am. Chem. Soc., 2001, 123, 1531;
18. (b) A. M. Hafez, A. E. Taggi, H. Wack, J. Esterbrook and T. Lectka, Org. Lett., 2001, 3, 2049;
19. (c) S. France, H. Wack, A. E. Taggi, A. M. Hafez, T. R. Wagerle, M. H. Shah, C. L. Dusich and T. Letcka, J. Am. Chem. Soc., 2004, 126, 4245.
20. (a) M. P. Brouchu, S. P. Brown and D. W. C. MacMillan, J. Am. Chem. Soc., 2004, 126, 4108;
21. (b) N. Halland, A. Braunton, S. Bachmann, M. Marigo and K. A. Jørgensen, J. Am. Chem. Soc., 2004, 126, 4790;
22. (c) M. Marigo, S. Bachmann, N. Halland, A. Braunton and K. A. Jørgensen, Angew. Chem. Int. Ed., 2004, 43, 5507.
23. (a) R. Engel, Chem. Rev., 1977, 77, 349;
24. (b) D. F. Wiemer, Tetrahedron, 1997, 53, 16609.
25. See e.g.: (a) P. Kafarski and B. Lejczak, Phosphorus, Sulfur Silicon Relat. Elem., 1991, 63, 193;
26. (b) V. Gouverneur and M. N. Lalloz, Tetrahedron Lett., 1996, 37, 6331;
27. (c) for examples of naturally occurring, and applications of different α-amino phosphonates/phosphonic acids see: Aminophosphonic and Aminophosphinic Acids, Chemistry and Biological Activity, ed. V. P. Kukhar and H. R. Hudson, John Wiley & Sons, New York, 2000.
28. For the formation of racemic fluoro esters see e.g.: H.-J. Tsai, A. Thenappan and D. J. Brown, J. Org. Chem., 1994, 59, 7085.
29. See e.g.: (a) M. G. Blackburn, Chem. Ind. (London), 1981, 134;
30. (b) D. J. Burton, Z.-Y. Yang and W. Qiu, Chem. Rev., 1996, 96, 1641;
31. (c) J. T. Welch, Fluorine in Bioorganic Chemistry, Wiley, New York, 1991;
32. (d) D. B. Berkowitz, M. Bose, T. J. Pfannenstiel and T. Doukov, J. Org. Chem., 2000, 65, 4498 and references therein.
33. See e.g.: (a) D. O'Hagan and H. S. Rzepa, Chem. Commun., 1997, 645;
34. (b) L. Chen, L. Wu, A. Otaka, M. S. Smyth, P. P. Roller, T. R. Burke, J. den Hertog and Z.-Y. Zhang, Biochem. Biophys. Res. Commun., 1995, 216, 976;
35. (c) G. R. J. Thatcher and A. S. Campbell, J. Org. Chem., 1993, 58, 2272;
36. (d) J. D. Dunitz and R. Taylor, Chem. Eur. J., 1997, 3, 89.
37. S. Kanemasa, Y. Oderaotoshi, S.-i. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada and D. P. Curran, J. Am. Chem. Soc., 1998, 120, 3074.
38. (a) H. Nishiyama, H. Sakaguchi, T. Nakamura, M. Horihata, M. Kondo and K. Itoh, Organometallics, 1989, 8, 846;
39. (b) G. Desimoni, G. Faita and P. Quadrelli, Chem. Rev., 2003, 103, 3119.