4-(4,6-Di[2,2,2-trifluoroethoxy]-1,3,5-triazin-2-yl)-4-methylomorpholinium tetrafluoroborate. Triazine-based coupling reagents designed for coupling sterically hindered substrates

Journal of Organic Chemistry

Volumn 76, Issue 11, 2011, Pages 4506-4513

  Jastrzabek, Konrad G ^a,b   Subiros Funosas, Ramon ^b   Albericio, Fernando ^b   Kolesinska, Beata ^a   Kaminski, Zbigniew J ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOISOBUTYRIC ACID; CONTROLLING EFFICIENCY; COUPLING PROCESS; CYCLIC TRANSITIONS; LEAVING GROUPS; REACTION CONDITIONS; STERIC HINDRANCES; TETRAFLUOROBORATES; THORPE-INGOLD EFFECT; TRIAZINE-BASED COUPLING REAGENTS;

AMINO ACIDS; CARBOXYLIC ACIDS; EFFICIENCY; RESINS;

SYNTHESIS (CHEMICAL);

2 (1H BENZOTRIAZOLE 1 YL) 1,1,3,3 TETRAMETHYLURONIUMTETRAFLUOROBORATE; 2 ACYLOXY 4,6 DI[2,2,2 TRIFLUOROETHOXY] 1,3,5 TRIAZINE; 2 CHLORO 4,6 DI(2,2,2 TRIFLUOROETHOXY) 1,3,5 TRIAZINE; 2,2 DIMETHYLPROPIONIC ACID 4,6 DI[2,2,2 TRIFLUOROETHOXY] [1,3,5]TRIAZIN 2 YL] ESTER; 4 [4,6 DI[2,2,2 TRIFLUOROETHOXY] 1,3,5 TRIAZIN 2 YL] 4 METHYLOMORPHOLINIUM TETRAFLUOROBORATE; 4 METHOXYBENZOIC ACID 4,6 DI[2,2,2 TRIFLUOROETHOXY] [1,3,5]TRIAZIN 2 YL; ANISIC ACID; CARBOXYLIC ACID; ENKEPHALIN; LEUCINE; SOLVENT; TETRAMETHYLUREA; TRIAZINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; SOLID PHASE SYNTHESIS; SOLVATION; SUBSTITUTION REACTION; SYNTHESIS;

ALKYLATION; AMINO ACIDS; BORATES; INDICATORS AND REAGENTS; MORPHOLINES; NITROGEN; OLIGOPEPTIDES; TRIAZINES;

EID: 79957802492     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2002038     Document Type: Article

References (40)

1. Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243
2. Albericio, F.; Chinchilla, R.; Dodsworth, D. J.; Najera, C. Org. Prep. Proced. Int. 2001, 33, 203
3. Han, S.-Y.; Kim, Y.-A. Tetrahedron 2004, 60, 2447
4. Montalbetti, C. A. G. N.; Falque, V. Tetrahedron 2005, 61, 10827
5. Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606
6. Bacsa, B.; Horvati, K.; Bosze, S.; Andreae, F.; Kappe, C. O. J. Org. Chem. 2008, 73, 7532
7. Sewald, N. Angew. Chem., Int. Ed. 2002, 41, 4661
8. Nishiuchi, Y.; Nishio, H.; Ishimaru, M.; Kimura, T. Int. J. Pept. Res. Ther. 2007, 13, 119
9. Sabatino, G.; Mulinacci, B.; Alcaro, M. C.; Chelli, M.; Rovero, P.; Papini, A. M. Lett. Pept. Sci. 2002, 9, 119
10. Santagada, V.; Fiorino, F.; Perissutti, E.; Severino, B.; De Filippis, V.; Vivenzio, B.; Caliendo, G. Tetrahedron Lett. 2001, 42, 5171
11. Wehrstedt, K. D.; Wandrey, P. A.; Heitkamp, D. J. Hazard. Mater. 2005, 126, 1
12. El-Faham, A.; Funosas, R. S.; Prohens, R.; Albericio, F. Chem.-Eur. J. 2009, 15, 9404
13. Subiros-Funosas, R.; Prohens, R.; Barbas, R.; El-Faham, A.; Albericio, F. Chem.-Eur. J. 2009, 15, 9394
14. El-Faham, A.; Albericio, F. Org. Lett. 2007, 9, 4475
15. El-Faham, A.; Albericio, F. J. Org. Chem. 2008, 73, 2731
16. Dutta, A. S.; Morley, J. S. J. Chem. Soc. (C) 1971, 2896
17. Albericio, F.; Bailen, M. A.; Chinchilla, R.; Dodsworth, D. J.; Najera, C. Tetrahedron 2001, 57, 9607
18. Garner, P.; Sesenoglu, O.; Kaniskan, H. U. Tetrahedron Lett. 2006, 47, 483
19. Kamiński, Z. J. Biopolymers 2000, 55, 140
20. Kamiński, Z. J.; Kolesińska, B.; Kolesińska, J.; Sabatino, G.; Chelli, M.; Rovero, P.; Blaszczyk, M.; Glówka, M. L.; Papini, A. M. J. Am. Chem. Soc. 2005, 127, 16912
21. Kolesińska, B.; Kamiński, Z. J. Org. Lett. 2009, 11, 765
22. Kolesińska, B.; Kasperowicz, K.; Sochacki, M.; Mazur, A.; Jankowski, S.; Kamiński, Z. J. Tetrahedron Lett. 2010, 51, 20
23. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397
24. Glowka, M. L.; Iwanicka, I.; Kaminski, Z. J. Acta Crystallogr. 1990, C46, 2211
25. Glówka, M. L.; Kamiński, Z. J.; Sobańska, A. W. Pol. J. Chem. 1994, 68, 1731
26. Jung, M. E.; Piizzi, G. Chem. Rev. 2005, 105, 1735
27. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858
28. Bruice, T. C.; Pandit, U. K. Proc. Natl. Acad. Sci. U.S.A. 1960, 46, 402
29. Jung, M. E.; Nichols, C. J. Tetrahedron Lett. 1996, 37, 7667
30. Jung, M. E. Synlett 1999, 843
31. Page, M. J.; Jencks, W. P. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1678
32. Kamiński, Z. J.; Paneth, P.; OLeary, M. J. Org. Chem. 1991, 56, 5716
33. Kaminski, Z. J.; Kolesińska, B.; Kolesińska, J.; Jastrzabek, K.; Papini, A.M. l; Bianchini, R.; Sabatino, G. Patent WO/2007/051496 from 2007. 05. 10.
34. Raw, S. A. Tetrahedron Lett. 2009, 50, 946
35. Carpino, L. A.; El-Faham, A. Tetrahedron 1999, 55, 6813
36. Subiros-Funosas, R.; Prohens, R.; Barbas, R.; El-Faham, A.; Albericio, F. Chem.-Eur. J. 2009, 15, 9394
37. Li, P.; Xu, J. C. Tetrahedron Lett. 1999, 40, 8301-8304
38. Kolesinska, B.; Kaminski, Z. J. Org. Lett. 2009, 11, 765-768
39. Luebke, K.; Schroeder, E. Ann. Chem. 1963, 665, 205-212
40. Mohapatra, D. K.; Datta, A. J. Org. Chem. 1999, 64, 6879-6880