Utilization of aminophosphonates in the petasis boronic acid mannich reaction

Synlett

Volumn , Issue 1, 2010, Pages 73-76

  Shevchuk, Michael V ^a,b   Sorochinsky, Alexander E ^a   Khilya, Volodymyr P ^b   Romanenko, Vadim D ^a   Kukhar, Valery P ^a  

^a INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

^b TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

Author keywords

Amino acids; Aminophosphonates; Boronic acids; Multicomponent reaction; Stereoselective synthesis

Indexed keywords

BETA AMINO ALPHA,ALPHA DIFLUOROMETHYLPHOSPHONATE; BORONIC ACID DERIVATIVE; GLYCINE DERIVATIVE; N PHOSPHONOMETHYLGLYCINE DERIVATIVE; NITROGEN; PHOSPHORAMIDIC ACID DERIVATIVE; PHOSPHORUS; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; MANNICH REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 77951684612     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218386     Document Type: Article

References (24)

1. (a) Multicomponent Reactions; Zhu, J.; Bienaymé, H., Eds.; Wiley-VCH: Weinheim, 2005.
2. (b) Yus, M.; Ramón, D. J. Angew. Chem. Int. Ed. 2005, 44, 1602.
3. (c) Dömling, A. Chem. Rev. 2006, 106, 17.
4. (d) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168.
5. (e) Simon, C.; Constantieux, T.; Rodriguez, J. Eur. J. Org. Chem. 2004, 4957.
6. (a) Petasis, N. A.; Akritopoulou, I. Tetrahedron Lett. 1993, 34, 583.
7. (b) Petasis, N. A.; Goodman, A.; Zavialov, I. A. Tetrahedron 1997, 53, 16463.
8. (c) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798.
9. (d) Petasis, N. A. Aust. J. Chem. 2007, 60, 795.
10. Petasis, N. A. In Multicomponent Reactions; Zhu, J.; Bienaymé, H., Eds.; Wiley-VCH: Weinheim, 2005, 199-223.
11. Southwood, T. J.; Curry, M. C.; Hutton, C. A. Tetrahedron 2006, 62, 236.
12. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445.
13. Petasis, N. A.; Zavialov, I. A. US 6, 232, 467, 2001.
14. Aminophosphonic and Aminophosphinic Acids; Kukhar, V. P.; Hudson, H. R., Eds.; John Wiley and Sons: Chichester, 2000.
15. (a) Kafarski, P.; Lejczak, B. Curr. Med. Chem. 2001, 1, 301.
16. (b) Ordóñez, M.; Rogas-Cabrera, H.; Cativiela, C. Tetrahedron 2009, 65, 17.
17. (c) Palacios, F.; Alonso, C.; de los Santos, J. M. Chem. Rev. 2005, 105, 899.
18. (d) Romanenko, V. D.; Kukhar, V. P. Chem. Rev. 2006, 106, 3868.
19. (e) Moonen, K.; Laureyn, I.; Stevens, C. V. Chem. Rev. 2004, 104, 6177.
20. (f) Mikolajczyk, M.; Balczewski, P. Top. Curr. Chem. 2003, 223, 161.
21. Candeias, N. R.; Veiros, L. F.; Afonso, C. A. M.; Gois, P. M. P. Eur. J. Org. Chem. 2009, 1859.
22. 2S: C, 44.72; H, 6.46, N, 2.90, S, 6.63. Found: C, 44.61; H, 6.41; N, 2.87; S, 6.68.
23. Röschenthaler, G.-V.; Kukhar, V. P.; Belik, M. Yu.; Mazurenko, K. I.; Sorochinsky, A. E. Tetrahedron 2006, 62, 9902.
24. 5P: C, 59.10; H, 6.04. Found: C, 59.06; H, 6.14.