Catalytic enantioselective trifluoromethylthiolation of oxindoles using shelf-stable N-(trifluoromethylthio)phthalimide and a cinchona alkaloid catalyst

Chemical Communications

Volumn 50, Issue 19, 2014, Pages 2508-2511

  Rueping, Magnus ^a   ByrLiune, Xiangqian ^a   Bootwicha, Teerawut ^a   Pluta, Roman ^a   Merkens, Carina ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CINCHONA ALKALOIDS; INDOLES; PHTHALIMIDES; STEREOISOMERISM;

CINCHONA ALKALOID; OXINDOLE; PHTHALIMIDE;

ARTICLE; CATALYST; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; CRYSTAL STRUCTURE; ELECTRON TRANSPORT; ELECTROPHILICITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; TRIFLUOROMETHYLTHIOLATION;

EID: 84893837623     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc49877h     Document Type: Article

References (68)

1. Selective Fluorination in Organic and Bioorganic Chemistry, ed. J. T. Welch, ACS Symposium Series, Washington, D.C., 1991.
2. V. A. Soloshonok, Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets, John Wiley & Sons Ltd., New York, 1999.
3. Organofluorine Compounds, Chemistry and Applications, ed. T. Hiyama, Springer, New York, 2000.
4. P. Kirsch, Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, Wiley-VCH, Weinheim, 2004.
5. K. Müller, C. Faeh, F. Diederich, Science, 2007, 317, 1881.
6. D. O'Hagan, Chem. Soc. Rev., 2008, 37, 308.
7. G. K. S. Prakash, F. Wang, Chimica Oggi-Chemistry Today, 2013, 30, 30.
8. C. Bobbio, V. Gouverneur, Org. Biomol. Chem., 2006, 4, 2065.
9. J.-A. Ma, D. Cahard, Chem. Rev., 2008, 108, PR1.
10. D. Cahard, X. Xu, S. Couve-Bonnaire, X. Pannecoucke, Chem. Soc. Rev., 2010, 39, 558.
11. S. Lectard, Y. Hamashima, M. Sodeoka, Adv. Synth. Catal., 2010, 352, 2708.
12. G. Valero, X. Companyó, R. Rios, Chem. Eur. J., 2011, 17, 2018.
13. C. Ni, J. Hu, Synlett, 2011, 770.
14. T. Furuya, A. S. Kamlet, T. Ritter, Nature, 2011, 473, 470.
15. T. Liang, C. N. Neumann, T. Ritter, Angew. Chem., Int. Ed., 2013, 52, 8214.
16. D. Parmar, M. S. Maji, M. Rueping, Chem.Eur. J., 2014, 20, 83.
17. M. Rueping, T. Bootwicha, S. Kambutong, E. Sugiono, Chem.Asian J., 2012, 7, 1195.
18. R. Husmann, E. Sugiono, S. Mersmann, G. Raabe, M. Rueping, C. Bolm, Org. Lett., 2011, 13, 1044.
19. M. Rueping, M. Stoeckel, E. Sugiono, T. Theissmann, Tetrahedron, 2010, 66, 6565.
20. M. Rueping, T. Theissmann, A. Kuenkel, R. M. Koenigs, Angew. Chem., Int. Ed., 2008, 47, 6798-6801.
21. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, ed. R. Filler, Y. Kobayashi and L. M. Yagupolskii, Elsevier, Amsterdam, 1993.
22. M. Morgenthaler, E. Schweizer, A. Hoffmann-Röder, F. Benini, R. E. Martin, G. Jaeschke, B. Wagner, H. Fischer, S. Bendels, D. Zimmerli, J. Schneider, F. Diederich, M. Kansy, K. Müller, ChemMedChem, 2007, 2, 1100.
23. Current Fluoroorganic Chemistry. New Synthetic Directions, Technologies, Materials and Biological Applications, ed. V. A. Soloshonok, K. Mikami, T. Yamazaki, J. T. Welch and J. Honek, ACS Symposium Series 949, Oxford University Press, 2007.
24. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev., 2008, 37, 320.
25. K. L. Kirk, Org. Process Res. Dev., 2008, 12, 305.
26. J.-P. Bégué and D. Bonnet-Delpon, Bioorganic and Medicinal Chemistry of Fluorine, Wiley-VCH, Hoboken, NJ, 2008.
27. W. K. Hagmann, J. Med. Chem., 2008, 51, 4359.
28. Fluorine in Medicinal Chemistry and Chemical Biology, ed. I. Ojima, Wiley-Blackwell, Chichester, 2009.
29. A. Leo, C. Hansch, D. Elkins, Chem. Rev., 1971, 71, 525.
30. C. Hansch, A. Leo, S. H. Unger, K. H. Kim, D. Nikaitani, E. J. Lien, J. Med. Chem., 1973, 16, 1207.
31. F. Leroux, P. Jeschke, M. Schlosser, Chem. Rev., 2005, 105, 827.
32. V. N. Boiko, Beilstein J. Org. Chem., 2010, 6, 880.
33. A. Tlili, T. Billard, Angew. Chem., Int. Ed., 2013, 52, 6818.
34. H. Liu, X. Jiang, Chem. Asian J., 2013, 8, 2546.
35. Q.-Y. Chen, J.-X. Duan, J. Chem. Soc., Chem. Commun., 1993, 918.
36. D. J. Adams, J. H. Clark, J. Org. Chem., 2000, 65, 1456.
37. D. J. Adams, A. Goddard, J. H. Clark, D. J. Macquarrie, Chem. Commun., 2000, 987.
38. W. Tyrra, D. Naumann, B. Hoge, Y. L. Yagupolskii, J. Fluorine Chem., 2003, 119, 101.
39. G. Teverovskiy, D. S. Surry, S. L. Buchwald, Angew. Chem., Int. Ed., 2011, 50, 7312.
40. C.-P. Zhang, D. A. Vicic, J. Am. Chem. Soc., 2012, 134, 183.
41. C. Chen, Y. Xie, L. Chu, R.-W. Wang, X. Zhang, F.-L. Qing, Angew. Chem., Int. Ed., 2012, 51, 2492.
42. C.-P. Zhang, D. A. Vicic, Chem. Asian J., 2012, 7, 1756.
43. L. D. Tran, I. Popov, O. Daugulis, J. Am. Chem. Soc., 2012, 134, 18237.
44. Z. Weng, W. He, C. Chen, R. Lee, D. Tan, Z. Lai, D. Kong, Y. Yuan, K.-W. Huang, Angew. Chem., Int. Ed., 2013, 52, 1548.
45. M. Rueping, N. Tolstoluzhsky, P. Nikolaienko, Chem. Eur. J., 2013, 19, 14043.
46. D. Kong, Z. Jiang, S. Xin, Z. Bai, Y. Yuan, Z. Weng, Tetrahedron, 2013, 69, 6046.
47. C. Chen, L. Chu, F.-L. Qing, J. Am. Chem. Soc., 2012, 134, 12454.
48. S. Munavalli, D. K. Rohrbaugh, D. I. Rossman, F. J. Berg, G. W. Wagner, H. D. Durst, Synth. Commun., 2000, 30, 2847.
49. R. Pluta, P. Nikolaienko, M. Rueping, Angew. Chem., Int. Ed., 2013, doi:10.1002/anie.201307484.
50. A. Ferry, T. Billard, B. R. Langlois, E. Bacqué, J. Org. Chem., 2008, 73, 9362.
51. A. Ferry, T. Billard, B. R. Langlois, E. Bacqué, Angew. Chem., Int. Ed., 2009, 48, 8551.
52. A. Ferry, T. Billard, E. Bacqué, B. R. Langlois, J. Fluorine Chem., 2012, 134, 160.
53. F. Baert, J. Colomb, T. Billard, Angew. Chem., Int. Ed., 2012, 51, 10382.
54. J. Liu, L. Chu, F.-L. Qing, Org. Lett., 2013, 15, 894.
55. S. Alazet, L. Zimmer, T. Billard, Angew. Chem., Int. Ed., 2013, 52, 10814.
56. Q. Xiao, J. Sheng, Z. Chen, J. Wu, Chem. Commun., 2013, 49, 8647.
57. J. Sheng, S. Li, J. Wu, Chem. Commun., 2014, 50, 578.
58. S. Alazet, K. Ollivier, T. Billard, Beilstein J. Org. Chem., 2013, 9, 2354.
59. X. Shao, X. Wang, T. Yang, L. Lu, Q. Shen, Angew. Chem., Int. Ed., 2013, 52, 3457.
60. Y.-D. Yang, A. Azuma, E. Tokunaga, M. Yamasaki, M. Shiro, N. Shibata, J. Am. Chem. Soc., 2013, 135, 8782.
61. T. Bootwicha, X. Liu, R. Pluta, I. Atodiresei, M. Rueping, Angew. Chem., Int. Ed., 2013, 52, 12856.
62. X. Wang, T. Yang, X. Cheng, Q. Shen, Angew. Chem., Int. Ed., 2013, 52, 12860.
63. Q.-H. Deng, C. Rettenmeier, H. Wadepohl, L. H. Gade, Chem. Eur. J., 2014, 20, 93.
64. S. Hibino, T. Choshi, Nat. Prod. Rep., 2001, 18, 66.
65. B. S. Jensen, CNS Drug Rev., 2002, 8, 353.
66. H. Lin, S. J. Danishefsky, Angew. Chem., Int. Ed., 2003, 42, 36.
67. A. B. Dounay, L. E. Overman, Chem. Rev., 2003, 103, 2945.
68. C. V. Galliford, K. A. Scheidt, Angew. Chem., Int. Ed., 2007, 46, 8748.