Asymmetric construction of fluorinated imidazolidines via Cu(i)-catalyzed exo′-selective 1,3-dipolar cycloaddition of azomethine ylides with fluorinated imines

Chemical Communications

Volumn 49, Issue 56, 2013, Pages 6277-6279

  Li, Qing Hua ^a   Wei, Liang ^a   Chen, Xuan ^a   Wang, Chun Jiang ^a,b  

^a WUHAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE YLIDE; COPPER; FLUORINATED IMINE; FLUORINE DERIVATIVE; IMIDAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG; FLUORINATED IMIDAZOLIDINE DERIVATIVE; FLUORINATED IMINE DERIVATIVE; IMINE; AZO COMPOUND; AZOMETHINE; THIOSEMICARBAZONE DERIVATIVE;

1,3 DIPOLAR CYCLOADDITION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; ENANTIOSELECTIVITY; CHEMISTRY; CYCLIZATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AZO COMPOUNDS; CATALYSIS; COPPER; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; IMIDAZOLIDINES; IMINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; THIOSEMICARBAZONES;

EID: 84880857802     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc43025a     Document Type: Article

References (32)

1. Fluorine in Medicinal Chemistry and Chemical Biology, ed. I. Ojima, Wiley-Blackwell, New York, 2009
2. J.-P. Bégué; and D. Bonnet-Delpon, Bioorganic and Medicinal Chemistry of Fluorine, John Wiley & Sons, Inc., New York, 2008
3. Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications, ed. V. A. Petrov, Wiley, Hoboken, New Jersey, 2009
4. Fluorine Containing Amino Acids-Synthesis and Properties, ed. V. P. Kukhar and V. A. Soloshonok, Wiley, Chichester, 1995
5. K. Uneyama, in Enantiocontrolled Synthesis of Fluoro-Organic Compounds, ed. V. A. Soloshonok, Wiley, Chichester, 1999, ch. 12
6. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev., 2008, 37, 320
7. R. Smits, C. D. Cadicamo, K. Burger, B. Koksch, Chem. Soc. Rev., 2008, 37, 1727
8. J. Nie, H.-C. Guo, D. Cahard, J.-A. Ma, Chem. Rev., 2010, 111, 455
9. G. F. Georgii, Fluorine-Containing Heterocycles. Part I. Synthesis by Intramolecular Cyclizationin Advances in Heterocyclic Chemistry, ed. A. R. Katritzky, Elsevier, Amsterdam, 2004
10. V. Sharma, M. S. Y. Khan, Eur. J. Med. Chem., 2001, 36, 651
11. V. Sharma, C. L. Crankshaw, D. Piwnica-Worms, J. Med. Chem., 1996, 39, 3483
12. C. R. Sage, M. D. Michelitsch, T. J. Stout, D. Biermann, R. Nissen, J. Finer-Moore, R. M. Stroud, Biochemistry, 1998, 37, 13893
13. J. Chang-Fong, K. Benamour, B. Szymonski, F. Thomasson, J.-M. Morand, M. Cussac, Chem. Pharm. Bull., 2000, 48, 729
14. A. Alexakis, P. Mangeney, N. Lensen, J.-P. Tranchier, R. Gosmini, S. Raussou, Pure Appl. Chem., 1996, 68, 531
15. A. Alexakis and P. Mangeney, in Advanced Asymmetric Synthesis, ed. G. R. Stephenson, Chapman and Hall, London, 1996
16. A. Erkkila, I. Majander, P. M. Pihko, Chem. Rev., 2007, 107, 5416
17. S. C. Zinner, W. A. Herrmann, F. E. Kühn, Tetrahedron: Asymmetry, 2008, 19, 1532
18. E.-K. Lee, S.-H. Kim, B.-H. Jung, W.-S. Ahn, G.-J. Kim, Tetrahedron Lett., 2003, 44, 1971
19. A. Prieto, N. Halland, K. A. Jorgensen, Org. Lett., 2005, 7, 3897
20. J. Yu, F. Shi, L.-Z. Gong, Acc. Chem. Res., 2011, 44, 1156
21. J. Adrio, J. C. Carretero, Chem. Commun., 2011, 47, 6784
22. L. M. Stanley, M. P. Sibi, Chem. Rev., 2008, 108, 2887
23. M. Alvarez-Corral, M. Munoz-Dorado, I. Rodrguez-Garca, Chem. Rev., 2008, 108, 3174
24. C. Nájera, J. M. Sansano, Angew. Chem., Int. Ed., 2005, 44, 6272
25. W.-J. Liu, X.-H. Chen, L.-Z. Gong, Org. Lett., 2008, 10, 5357
26. H. Xie, J. Zhu, Z. Chen, S. Li, Y. Wu, J. Org. Chem., 2010, 75, 7468
27. T. Arai, N. Yokoyama, A. Mishiro, H. Sato, Angew. Chem., Int. Ed., 2010, 49, 7895
28. A. Awata, T. Arai, Chem.Eur. J., 2012, 18, 8278
29. C.-J. Wang, G. Liang, Z.-Y. Xue, F. Gao, J. Am. Chem. Soc., 2008, 130, 17250
30. T.-L. Liu, Z.-L. He, H.-Y. Tao, Y.-P. Cai, C.-J. Wang, Chem. Commun., 2011, 47, 2616
31. T. Hayashi, T. Mise, M. Fukushima, M. Kagotani, N. Nagashima, Y. Hamada, A. Matsumoto, S. Kawakami, M. Konishi, K. Yamamoto, M. Kumada, Bull. Chem. Soc. Jpn., 1980, 53, 1138
32. A. Viso, R. F. de la Pradilla, M. Tortosa, A. García, A. Flores, Chem. Rev., 2011, 111, PR1