Synthesis and use of a trifluoromethylated azomethine ylide precursor

Journal of Organic Chemistry

Volumn 77, Issue 24, 2012, Pages 11071-11078

  Tran, Gaël ^a   Meier, Robin ^a   Harris, Lawrence ^b   Browne, Duncan L ^a   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b CALLAGHAN INNOVATION   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE YLIDES; BUILDING BLOCKES; FLUOROUS; PYRROLIDINES;

CHEMISTRY;

ORGANIC COMPOUNDS;

AZOMETHINE YLIDE; BRONSTED ACID; FLUORIDE; LEWIS ACID; METHYL GROUP; PYRROLE DERIVATIVE; PYRROLIDINE DERIVATIVE; PYRROLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; METHYLATION; OXIDATION REDUCTION REACTION; PRECURSOR; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION OPTIMIZATION; SCREENING; SYNTHESIS;

AZO COMPOUNDS; CHEMISTRY TECHNIQUES, SYNTHETIC; CHLOROFLUOROCARBONS, METHANE; STEREOISOMERISM; SUBSTRATE SPECIFICITY; THIOSEMICARBAZONES;

EID: 84871583825     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302052m     Document Type: Article

References (42)

1. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305-321
2. Lundgren, R. J.; Stradiotto, M. Angew. Chem., Int. Ed. 2010, 49, 9322-9324
3. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470-477
4. Besset, T.; Schneider, C.; Cahard, D. Angew. Chem., Int. Ed. 2012, 51, 5048-5050
5. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330
6. Jeschke, P. ChemBioChem 2004, 5, 570-589
7. Kirsch, P.; Bremer, M. Angew. Chem., Int. Ed. 2000, 39, 4216-4235
8. Knauber, T.; Arikan, F.; Röschenthaler, G.-V.; Gooßen, L. J. Chem.-Eur. J. 2011, 17, 2689-2697
9. Khan, B. A.; Buba, A. E.; Gooßen, L. J. Chem.-Eur. J. 2012, 18, 1577-1581
10. Zanardi, A.; Novikov, M. A.; Martin, E.; Benet-Buchholz, J.; Grushin, V. V. J. Am. Chem. Soc. 2011, 133, 20901-20913
11. Ji, Y.; Brueckl, T.; Baxter, R. D.; Fujiwara, Y.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 14411-14415
12. Oishi, M.; Kondo, H.; Amii, H. Chem. Commun. 2009, 1909-1911
13. Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224-228
14. Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648-3649
15. Mu, X.; Chen, S.; Zhen, X.; Liu, G. Chem.-Eur. J. 2011, 17, 6039-6042
16. Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 1298-1304
17. Fujiwara, Y.; Dixon, J. A.; Rodriguez, R. A.; Baxter, R. D.; Dixon, D. D.; Collins, M. R.; Blackmond, D. G.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 1494-1497
18. Tang, P.; Wang, W.; Ritter, T. J. Am. Chem. Soc. 2011, 133, 11482-11484
19. Huang, C.; Liang, T.; Harada, S.; Lee., E.; Ritter, T. J. Am. Chem. Soc. 2011, 133, 13308-13310
20. Teverovskiy, G.; Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 7312-7314
21. Novák, P.; Lishchynskyi, A.; Grushin, V. V. Angew. Chem., Int. Ed. 2012, 51, 7767-7770
22. Wilson, P. G.; Percy, J. M.; Redmond, J. M.; McCarter, A. W. J. Org. Chem. 2012, 77, 6384-6393
23. Kyne, S. H.; Percy, J. M.; Pullin, R. D. C.; Redmond, J. M.; Wilson, P. G. Org. Biomol. Chem. 2011, 9, 8328-8339
24. Audouard, C.; Garayt, M. R.; Kérouréden, E.; Percy, J. M.; Yang, H. J. Fluor. Chem. 2005, 126, 611-623
25. Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863-909
26. Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765-2809
27. Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484-4517
28. Li, Q.-H.; Xue, Z.-Y.; Tao, H.-Y.; Wang, C.-J. Tetrahedron Lett. 2012, 53, 3650-3653
29. Hernández-Toribio, J.; Padilla, S.; Adrio, J.; Carretero, J. C. Angew. Chem., Int. Ed. 2012, 51, 8854
30. Burger, K.; Meffert, A.; Bauer, S. J. Fluor. Chem. 1977, 10, 57-62
31. Tanaka, K.; Nagatani, S.; Ohsuga, M.; Mitsuhashi, K. Bull. Chem. Soc. Jpn. 1994, 67, 589-591
32. Tanaka, K.; Ohsuga, M.; Sugimoto, Y.; Okafuji, Y.; Mitsuhashi, K. J. Fluorine Chem. 1988, 39, 39-45
33. Laduron, F.; Ates, C.; Viehe, H. G. Tetrahedron Lett. 1996, 37, 5515-5518
34. Laduron, F.; Viehe, H. G. Tetrahedron 2002, 58, 3543-3551
35. Domingo, L. R. J. Org. Chem. 1999, 64, 3922-3929
36. Mimura, H.; Kawada, K.; Yamashita, T.; Sakamoto, T.; Kikugawa, Y. J. Fluorine Chem. 2010, 131, 477-486
37. Gerlach, K.; Hoffmann, H. M. R.; Wartchow, R. J. Chem. Soc., Perkin Trans. 1 1988, 3867-3872
38. Padwa, A.; Dent, W. J. Org. Chem. 1987, 52, 235-244
39. Padwa, A.; Chen, Y. Tetrahedron Lett. 1983, 24, 3447-3450
40. Terao, Y.; Kotaki, H.; Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1985, 33, 896-898
41. Hosomi, A.; Sakata, Y.; Sakurai, H. Chem. Lett. 1984, 1117-1120
42. Carey, J. S. J. Org. Chem. 2001, 66, 2526-2529