N-heterocyclic carbene catalyzed nucleophilic acylation of trifluoromethyl ketimines

Synthesis

Volumn , Issue 24, 2009, Pages 4125-4128

  Enders, Diester ^a   Henseler, Alexander ^a   Lowins, Sebastian ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

amino trifluoromethyl ketones; Aldehyde ketimine cross coupling; N heterocyclic carbenes; Organocatalysis; Umpolung

Indexed keywords

CROSS-COUPLINGS; N-HETEROCYCLIC CARBENES; ORGANOCATALYSIS; TRIFLUOROMETHYLKETONE; UMPOLUNG;

ACYLATION; CARBON INORGANIC COMPOUNDS; KETONES; RATE CONSTANTS; REACTION KINETICS;

CATALYSIS;

1 (4,5 DIMETHYLFURAN 2 YL) 3,3,3 TRIFLUORO 2 PHENYL 2 (PHENYLAMINO)PROPAN 1 ONE; 1 (BENZOFURAN 2 YL) 3,3,3 TRIFLUORO 2 PHENYL 2 (PHENYLAMINO)PROPAN 1 ONE; 1 [5 (4 CHLOROPHENYL)FURAN 2 YL] 3,3,3 TRIFLUORO 2 PHENYL 2 (PHENYLAMINO)PROPAN 1 ONE; 2 (4 BROMOPHENYL) 3,3,3 TRIFLUORO 1 (FURAN 2 YL) 2 (4 METHOXYPHENYLAMINO)PROPAN 1 ONE; 2 (4 CHLOROPHENYL) 3,3,3 TRIFLUORO 1 (FURAN 2 YL) 2 (PHENYLAMINO)PROPAN 1 ONE; 3,3,3 TRIFLUORO 1 (5 METHYLFURAN 2 YL) 2 PHENYL 2 (PHENYLAMINO)PROPAN 1 ONE; 3,3,3 TRIFLUORO 1 (FURAN 2 YL) 2 (4 METHOXYPHENYLAMINO) 2 PHENYLPROPAN 1 ONE; 3,3,3 TRIFLUORO 1 (FURAN 2 YL) 2 PHENYL 2 (PHENYLAMINO)PROPAN 1 ONE; ANILINE DERIVATIVE; CARBENE; IMINE; N [1 (4 CHLOROPHENYL) 2,2,2 TRIFLUOROETHYLIDENE]ANILINE; N HETEROCYCLIC CARBENE; TRIFLUOROMETHYL KETIMINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CROSS COUPLING REACTION; DISTILLATION; ENANTIOSELECTIVITY; MELTING POINT; NUCLEOPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION;

EID: 77955807154     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217070     Document Type: Article

References (33)

1. For reviews, see: (a) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606.
2. (b) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
3. (c) Rovis, T. Chem. Lett. 2008, 2
4. (d) Marion, N.; Diez-Gonzalez, S.; Nolan, S. P. Angew. Chem. Int. Ed. 2007, 46, 2988;
5. Angew. Chem. 2007, 119, 3046
6. (e) Christmann, M. Angew. Chem. Int. Ed. 2005, 44, 2632;
7. Angew. Chem. 2005, 117, 2688
8. (f) Zeitler, K. Angew. Chem. Int. Ed. 2005, 44, 7506;
9. Angew. Chem. 2005, 117, 7674.
10. (g) Enders, D.; Narine, A. A. J. Org. Chem. 2008, 73, 7857.
11. Wöhler, F.; Liebig, J. Ann. Pharm. 1832, 3, 249
12. For selected examples of inter-, and intramolecular and enantioselective benzoin reactions, see: (a) Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem. Int. Ed. 2006, 45, 1463;
13. Angew. Chem. 2006, 118, 1491.
14. (b) Enders, D.; Niemeier, O.; Raabe, G. Synlett 2006, 2431
15. (c) Takikawa, H.; Hachisu, Y.; Bode, J. W.; Suzuki, K. Angew. Chem. Int. Ed. 2006, 45, 3492;
16. Angew. Chem. 2006, 118, 3572.
17. (d) Enders, D.; Niemeier, O. Synlett 2004, 2111.
18. (e) Hachisu, Y.; Bode, J. W.; Suzuki, K. Adv. Synth. Catal. 2004, 346, 1097.
19. (f) Hachisu, Y.; Bode, J. W.; Suzuki, K. J. Am. Chem. Soc. 2003, 125, 8432.
20. (g) Enders, D.; Kallfass, U. Angew. Chem. Int. Ed. 2002, 41, 1743;
21. Angew. Chem. 2002, 114, 1822.
22. Di Gioia, M. L.; Leggio, A.; Liguori, A.; Napoli, A.; Siciliano, C.; Sindona, G. J. Org. Chem. 2001, 66, 7002; and references therein.
23. (a) He, M.; Bode, J. W. Org. Lett. 2005, 7, 3131.
24. (b) Mattson, A. E.; Scheidt, K. A. Org. Lett. 2004, 6, 4363.
25. Castells, J.; López-Calahorra, F.; Bassedas, M.; Urrios, P. Synthesis 1988, 314.
26. (a) Mennen, S. M.; Gipson, J. D.; Kim, Y. R.; Miller, S. J. J. Am. Chem. Soc. 2005, 127, 1654.
27. (b) Frantz, D. E.; Morency, L.; Soheili, A.; Murry, J. A.; Grabowski, E. J. J.; Tillyer, R. D. Org. Lett. 2004, 6, 843.
28. (c) Murry, J. A.; Frantz, D. E.; Soheili, A.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 9696.
29. Li, G.-Q.; Dai, L.-X.; You, S.-L. Chem. Commun. 2007, 852.
30. Enders, D.; Henseler, A. Adv. Synth. Catal. 2009, 351, 1749.
31. (a) Enders, D.; Han, J.; Henseler, A. Chem. Commun. 2008, 3989.
32. (b) Chiang, P.-C.; Kaeobamrung, J.; Bode, J. W. J. Am. Chem. Soc. 2007, 129, 3520
33. Stauffer, S. R.; Sun, J.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Bioorg. Med. Chem. 2000, 8, 1293.