N-trifluoromethylthiophthalimide: A stable electrophilic SCF 3-reagent and its application in the catalytic asymmetric trifluoromethylsulfenylation

Angewandte Chemie - International Edition

Volumn 52, Issue 49, 2013, Pages 12856-12859

  Bootwicha, Teerawut ^a   Liu, Xiangqian ^a   Pluta, Roman ^a   Atodiresei, Iuliana ^a   Rueping, Magnus ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

cinchona alkaloids; fluorine; indanones; organocatalysis; trifluoromethylsulfenylation

Indexed keywords

CINCHONA ALKALOID; ENANTIOSELECTIVE; INDANONES; ITS APPLICATIONS; ORGANOCATALYSIS; QUATERNARY CARBON; STEREOGENIC CENTERS; TRIFLUOROMETHYLSULFENYLATION;

ALKALOIDS; ENANTIOSELECTIVITY; FLUORINE; NITROGEN COMPOUNDS; REACTION KINETICS;

METABOLITES;

EID: 84888594105     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201304957     Document Type: Article

References (65)

1. Selective Fluorination in Organic and Bioorganic Chemistry (Ed.:, J. T. Welch,), ACS Symposium Series, Washington, 1991
2. V. A. Soloshonok, Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets, Wiley, 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, 1881-1886
6. D. O'Hagan, Chem. Soc. Rev. 2008, 37, 308-319.
7. For reviews of stereoselective formation of fluorinated compounds, see C. Bobbio, V. Gouverneur, Org. Biomol. Chem. 2006, 4, 2065-2075
8. J.-A. Ma, D. Cahard, Chem. Rev. 2008, 108, PR 1 -PR 43
9. D. Cahard, X. Xu, S. Couve-Bonnaire, X. Pannecoucke, Chem. Soc. Rev. 2010, 39, 558-568
10. S. Lectard, Y. Hamashima, M. Sodeoka, Adv. Synth. Catal. 2010, 352, 2708-2732
11. G. Valero, X. Companyõ, R. Rios, Chem. Eur. J. 2011, 17, 2018-2037
12. C. Ni, J. Hu, Synlett 2011, 770-782
13. T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470-477
14. T. Liang, C. N. Neumann, T. Ritter, Angew. Chem. 2013, 125, 8372-8423
15. Angew. Chem. Int. Ed. 2013, 52, 8214-8264.
16. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (Eds.:, R. Filler, Y. Kobayashi, L. M. Yagupolskii,), Elsevier, Amsterdam, 1993
17. 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, 1100-1115
18. Current Fluoroorganic Chemistry. New Synthetic Directions, Technologies, Materials and Biological Applications (Eds.:, V. A. Soloshonok, K. Mikami, T. Yamazaki, J. T. Welch, J. Honek,), ACS Symposium Series 949, Oxford University Press, 2007
19. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320-330
20. K. L. Kirk, Org. Process Res. Dev. 2008, 12, 305-321
21. J.-P. Bégué, D. Bonnet-Delpon, Bioorganic and Medicinal Chemistry of Fluorine, Wiley-VCH, Hoboken, NJ, 2008
22. W. K. Hagmann, J. Med. Chem. 2008, 51, 4359-4369
23. Fluorine in Medicinal Chemistry and Chemical Biology (Ed.:, I. Ojima,), Wiley-Blackwell, Chichester, 2009.
24. A. Leo, C. Hansch, D. Elkins, Chem. Rev. 1971, 71, 525-616
25. C. Hansch, A. Leo, S. H. Unger, K. H. Kim, D. Nikaitani, E. J. Lien, J. Med. Chem. 1973, 16, 1207-1216
26. F. Leroux, P. Jeschke, M. Schlosser, Chem. Rev. 2005, 105, 827-856.
27. V. N. Boiko, Beilstein J. Org. Chem. 2010, 6, 880-921
28. A. Tlili, T. Billard, Angew. Chem. 2013, 125, 6952-6954
29. Angew. Chem. Int. Ed. 2013, 52, 6818-6819
30. H. Liu, X. Jiang, Chem. Asian J. 2013, DOI:.
31. Q.-Y. Chen, J.-X. Duan, J. Chem. Soc. Chem. Commun. 1993, 918-919
32. D. J. Adams, J. H. Clark, J. Org. Chem. 2000, 65, 1456-1460
33. D. J. Adams, A. Goddard, J. H. Clark, D. J. Macquarrie, Chem. Commun. 2000, 987-988
34. W. Tyrra, D. Naumann, B. Hoge, Y. L. Yagupolskii, J. Fluorine Chem. 2003, 119, 101-107
35. G. Teverovskiy, D. S. Surry, S. L. Buchwald, Angew. Chem. 2011, 123, 7450-7452
36. Angew. Chem. Int. Ed. 2011, 50, 7312-7314
37. C.-P. Zhang, D. A. Vicic, J. Am. Chem. Soc. 2012, 134, 183-185
38. C. Chen, Y. Xie, L. Chu, R.-W. Wang, X. Zhang, F.-L. Qing, Angew. Chem. 2012, 124, 2542-2545
39. Angew. Chem. Int. Ed. 2012, 51, 2492-2495
40. C. Chen, L. Chu, F.-L. Qing, J. Am. Chem. Soc. 2012, 134, 12454-12457
41. C.-P. Zhang, D. A. Vicic, Chem. Asian J. 2012, 7, 1756-1758
42. Z. Weng, W. He, C. Chen, R. Lee, D. Tan, Z. Lai, D. Kong, Y. Yuan, K.-W. Huang, Angew. Chem. 2013, 125, 1588-1592
43. 3)], see
44. D. Kong, Z. Jiang, S. Xin, Z. Bai, Y. Yuan, Z. Weng, Tetrahedron 2013, 69, 6046-6050
45. J. Tan, G. Zhang, Y. Ou, Y. Yuan, Z. Weng, Chin. J. Chem. 2013, 31, 921-926.
46. W. A. Sheppard, J. Org. Chem. 1964, 29, 895-898
47. K. Bogdanowicz-Szwed, B. Kawalek, M. Lieb, J. Fluorine Chem. 1987, 35, 317-327.
48. S. Munavalli, D. K. Rohrbaugh, D. I. Rossman, F. J. Berg, G. W. Wagner, H. D. Durst, Synth. Commun. 2000, 30, 2847-2854.
49. A. Ferry, T. Billard, B. R. Langlois, E. Bacqué, J. Org. Chem. 2008, 73, 9362-9365
50. A. Ferry, T. Billard, B. R. Langlois, E. Bacqué, Angew. Chem. 2009, 121, 8703-8707
51. Angew. Chem. Int. Ed. 2009, 48, 8551-8555
52. L. D. Tran, I. Popov, O. Daugulis, J. Am. Chem. Soc. 2012, 134, 18237-18240
53. A. Ferry, T. Billard, E. Bacqué, B. R. Langlois, J. Fluorine Chem. 2012, 134, 160-163
54. F. Baert, J. Colomb, T. Billard, Angew. Chem. 2012, 124, 10528-10531
55. Angew. Chem. Int. Ed. 2012, 51, 10382-10385
56. J. Liu, L. Chu, F.-L. Qing, Org. Lett. 2013, 15, 894-897
57. Y.-D. Yang, A. Azuma, E. Tokunaga, M. Yamasaki, M. Shiro, N. Shibata, J. Am. Chem. Soc. 2013, 135, 8782-8785.
58. X. Shao, X. Wang, T. Yang, L. Lu, Q. Shen, Angew. Chem. 2013, 125, 3541-3544
59. Angew. Chem. Int. Ed. 2013, 52, 3457-3460.
60. E. Fillion, D. Fishlock, A. Wilsily, J. M. Goll, J. Org. Chem. 2005, 70, 1316-1327.
61. R. Marcia de Figueiredo, M. Christmann, Eur. J. Org. Chem. 2007, 2575-2600
62. E. Marqués-Lõpez, R. P. Herrera, M. Christmann, Nat. Prod. Rep. 2010, 27, 1138-1167.
63. CCDC 963612 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
64. This Communication is published back-to-back with the following study: X. Q. Wang, T. Yang, X. Cheng, Q. Shen, Angew. Chem. 2013, 125, 13098-13102;
65. Angew. Chem. Int. Ed. 2013, 52, 12860-12864.