An easy approach to optically active α-amino phosphonic acid derivatives by chiral Zn(II)-catalyzed enantioselective amination of phosphonates

Journal of the American Chemical Society

Volumn 127, Issue 16, 2005, Pages 5772-5773

  Bernardi, Luca ^a,b   Zhuang, Wei ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYL 2 OXO 2 PHENYLETHYL PHOSPHONIC ACID; CARBOXYLIC ACID DERIVATIVE; LEWIS ACID; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; ZINC ION;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; X RAY ANALYSIS;

AMINATION; AMINO ACIDS; AZO COMPOUNDS; CATALYSIS; DICARBOXYLIC ACIDS; KETONES; OXAZOLIDINONES; PHOSPHONIC ACIDS; STEREOISOMERISM; ZINC;

EID: 17744365584     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050989v     Document Type: Article

References (40)

1. (a) Kafarski, P.; Lejczak, B. Phosphorous, Sulfur Silicon Relat. Elem. 1991, 63, 193.
2. (b) Aminophosphonic and Aminophosphinic Acids; Kukhar, V. P., Hudson, H. R., Eds.; John Wiley & Sons, 2000.
3. (c) Palacios, F.; Alanso, C.; Sanros, J. Chem. Rev. 2005, 105, 899 (this is a review dealing with β-amino phosphonates).
4. (a) Atherton, F. R.; Hassall, C. H.; Lambert, R. W. J. Med. Chem. 1986, 29, 29.
5. (b) Hirschmann, R.; Smith, A. B., III; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengler, P. A.; Benkovic, S. J. Science 1994, 265, 234.
6. (c) Allen, J. G.; Atherton, F. R.; Hall, M. J.; Hassal, C. H.; Homes, S. W.; Lambert, R. W.; Nisbet, L. J.; Ringrose, P. S. Nature 1978, 272, 56.
7. (a) Ginnousis, P. P.; Bartleet, P. A. J. Med. Chem. 1987, 30, 1603.
8. (b) Allen, M. C.; Fuhrer, W.; Tuck, B.; Wade, R.; Wood, J. M. J. Med. Chem. 1989, 32, 1652.
9. (a) Peyman, A.; Budt, K.-H.; Spanig, J.; Stowasser, B.; Ruppert, D. Tetrahedron Lett. 1992, 33, 4549.
10. (b) Peyman, A.; Stahl, W.; Wagner, K.; Ruppert, D.; Budt, K.-H. Bioorg. Med. Chem. Lett. 1994, 4, 2601.
11. (c) Stowasser, B.; Budt, K.-H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625.
12. Haebich, D.; Hansen, J.; Paessens, A. Eur. Pat. Appl. EP 472077, 1992, Bayer A. G.; Chem. Abstr. 1992, 117, 27161z.
13. Haebich, D.; Hansen, J.; Paessens, A. Eur. Pat. Appl. EP 472077, 1992, Bayer A. G.; Chem. Abstr. 1992, 117, 27161z.
14. (e) Powers, J. C.; Boduszek, B.; Oleksyszyn, J. PCT Int. Appl. WO 95 29691, 1995, Georgia Technol. Research Corp.; Chem. Abstr. 1996, 124, 203102m.
15. Gröger, H.; Hammer, B. Chem.-Eur. J. 2000, 6, 943.
16. (a) Joly, G. D.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 4102.
17. (b) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656.
18. (c) Gröger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089.
19. (d) Schlemminger, I.; Saida, Y.; Gröger, H.; Maison, W.; Durot, N.; Sasai, H.; Shibasaki, M.; Martens, J. J. Org. Chem. 2000, 65, 4818.
20. (e) Gröger, H.; Saida, Y.; Arai, S.; Martens, J.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 9291.
21. (f) Davis, F. A.; Prasad, K. R. J. Org. Chem. 2003, 68, 7249 and references therein.
22. (a) Baldwin, I. C.; Williams, M. J.; Beckett, P. P. Tetrahedron: Asymmetry 1995, 6, 679.
23. (b) Sawamura, M.; Ito, J. Tetrahedron Lett. 1989, 30, 2247.
24. (c) Togni, A.; Pastor, S. D. Tetrahedron Lett. 1989, 30, 1071.
25. Kobayashi, S.; Kiyohara, H.; Nakamura, Y.; Matsubara, R. J. Am. Chem. Soc. 2004, 126, 6558.
26. (a) Hanessian, S.; Bennani, Y. L. Synthesis 1994, 1272.
27. (b) Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191.
28. (c) Pagliarin, R.; Papeo, G.; Sello, G.; Sisti, M. Tetrahedron 1996, 52, 13783.
29. (d) Jommi, G.; Miglierini, G.; Pagliarin, R.; Sello, G.; Sisti, M. Tetrahedron 1992, 48, 7275.
30. Reviews: (a) Greek, C.; Droillat, B.; Thomassigny, C. Eur. J. Org. Chem. 2004, 7, 1377. (b) Erlik, E. Tetrahedron 2004, 60, 8747. For chiral Lewis acid-catalyzed reactions, see: (c) Juhl, K.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 2420. (d) Marigo, M.; Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1367. (e) Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595.
31. Reviews: (a) Greek, C.; Droillat, B.; Thomassigny, C. Eur. J. Org. Chem. 2004, 7, 1377. (b) Erlik, E. Tetrahedron 2004, 60, 8747. For chiral Lewis acid-catalyzed reactions, see: (c) Juhl, K.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 2420. (d) Marigo, M.; Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1367. (e) Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595.
32. Reviews: (a) Greek, C.; Droillat, B.; Thomassigny, C. Eur. J. Org. Chem. 2004, 7, 1377. (b) Erlik, E. Tetrahedron 2004, 60, 8747. For chiral Lewis acid-catalyzed reactions, see: (c) Juhl, K.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 2420. (d) Marigo, M.; Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1367. (e) Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595.
33. Reviews: (a) Greek, C.; Droillat, B.; Thomassigny, C. Eur. J. Org. Chem. 2004, 7, 1377. (b) Erlik, E. Tetrahedron 2004, 60, 8747. For chiral Lewis acid-catalyzed reactions, see: (c) Juhl, K.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 2420. (d) Marigo, M.; Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1367. (e) Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595.
34. Reviews: (a) Greek, C.; Droillat, B.; Thomassigny, C. Eur. J. Org. Chem. 2004, 7, 1377. (b) Erlik, E. Tetrahedron 2004, 60, 8747. For chiral Lewis acid-catalyzed reactions, see: (c) Juhl, K.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 2420. (d) Marigo, M.; Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1367. (e) Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595.
35. For catalytic halogenation and Mannich reactions of β-keto phosphonates, see: (a) Bernardi, L.; Jørgensen, K. A. Chem. Commun 2005, 1324. (b) Hamashima, Y.; Suzuki, T.; Shimura, Y.; Shimazu, T.; Umebayashi, N.; Tamura, T.; Sesamoto, N.; Sodeoka, M. Tetrahedron Lett. 2005, 46, 1447. (c) Kjærsgaard, A.; Jørgensen, K. A. Org. Biomol. Chem. 2005, 3, 804.
36. For catalytic halogenation and Mannich reactions of β-keto phosphonates, see: (a) Bernardi, L.; Jørgensen, K. A. Chem. Commun 2005, 1324. (b) Hamashima, Y.; Suzuki, T.; Shimura, Y.; Shimazu, T.; Umebayashi, N.; Tamura, T.; Sesamoto, N.; Sodeoka, M. Tetrahedron Lett. 2005, 46, 1447. (c) Kjærsgaard, A.; Jørgensen, K. A. Org. Biomol. Chem. 2005, 3, 804.
37. For catalytic halogenation and Mannich reactions of β-keto phosphonates, see: (a) Bernardi, L.; Jørgensen, K. A. Chem. Commun 2005, 1324. (b) Hamashima, Y.; Suzuki, T.; Shimura, Y.; Shimazu, T.; Umebayashi, N.; Tamura, T.; Sesamoto, N.; Sodeoka, M. Tetrahedron Lett. 2005, 46, 1447. (c) Kjærsgaard, A.; Jørgensen, K. A. Org. Biomol. Chem. 2005, 3, 804.
38. For example, where HFIP was used in catalytic asymmetric reactions, see: (a) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Wills, M. C. J. Am. Chem. Soc. 2001, 123, 4480.
39. Kitamura, M.; Tokunaga, M.; Pham, T.; Lubell, W. D.; Noyori, R. Tetrahedron Lett. 1995, 36, 5769.
40. For an investigation of Lewis acid-bisoxazoline intermediates, see: Thorhauge, J.; Roberson, M.; Hazell, R. G.; Jørgensen, K. A. Chem.-Eur. J. 2002, 8, 1888.