Effective synthesis of chiral N-fluoroaryl aziridines through enantioselective aziridination of alkenes with fluoroaryl azides

Angewandte Chemie - International Edition

Volumn 52, Issue 20, 2013, Pages 5309-5313

  Jin, Li Mei ^a   Xu, Xue ^a   Lu, Hongjian ^a   Cui, Xin ^a   Wojtas, Lukasz ^a   Zhang, X Peter ^a  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

aryl azides; asymmetric catalysis; aziridines; cobalt; porphyrins

Indexed keywords

ARYL AZIDES; ASYMMETRIC CATALYSIS; AZIRIDINATION; AZIRIDINES; CATALYST LOADINGS; EFFECTIVE SYNTHESIS; ENANTIOSELECTIVE;

CATALYSTS; CHEMICAL REACTIONS; COBALT; COBALT COMPOUNDS; ENANTIOSELECTIVITY; NITROGEN COMPOUNDS; OLEFINS; PORPHYRINS;

LOADING;

ALKENE; AZIRIDINE DERIVATIVE; COBALT; FLUORINATED HYDROCARBON; METALLOPORPHYRIN;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; STEREOISOMERISM; SYNTHESIS;

ALKENES; AZIRIDINES; CATALYSIS; COBALT; HYDROCARBONS, FLUORINATED; HYDROGEN BONDING; METALLOPORPHYRINS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84877305359     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201209599     Document Type: Article

References (62)

1. P. Müller, C. Fruit, Chem. Rev. 2003, 103, 2905
2. H. Pellissier, Tetrahedron 2010, 66, 1509
3. T. G. Driver, Org. Biomol. Chem. 2010, 8, 3831
4. J. W. W. Chang, T. M. U. Ton, P. W. H. Chan, Chem. Rec. 2011, 11, 331.
5. T. Ibuka, Chem. Soc. Rev. 1998, 27, 145
6. J. B. Sweeney, Chem. Soc. Rev. 2002, 31, 247
7. A. K. Yudin, Acc. Chem. Res. 2006, 39, 194
8. P. Lu, Tetrahedron 2010, 66, 2549
9. S. Stankovic̈, M. D'Hooghe, S. Catak, H. Eum, M. Waroquier, V. Van Speybroeck, N. De Kimpe, H.-J. Ha, Chem. Soc. Rev. 2012, 41, 643
10. S. Florio, R. Luisi, Chem. Rev. 2010, 110, 5128
11. X. E. Hu, Tetrahedron 2004, 60, 2701
12. G. S. Singh, M. D'Hooghe, N. De Kimpe, Chem. Rev. 2007, 107, 2080.
13. T. Katsuki, Chem. Lett. 2005, 34, 1304
14. S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. 2005, 117, 5320
15. Angew. Chem. Int. Ed. 2005, 44, 5188
16. S. Fantauzzi, A. Caselli, E. Gallo, Dalton Trans. 2009, 5434
17. H. Lu, X. P. Zhang, Chem. Soc. Rev. 2011, 40, 1899.
18. V. Subbarayan, J. V. Ruppel, S. Zhu, J. A. Perman, X. P. Zhang, Chem. Commun. 2009, 4266
19. J. E. Jones, J. V. Ruppel, G.-Y. Gao, T. M. Moore, X. P. Zhang, J. Org. Chem. 2008, 73, 7260
20. C. Kim, T. Uchida, T. Katsuki, Chem. Commun. 2012, 48, 7188
21. L. Liang, H. Lv, Y. Yu, P. Wang, J.-L. Zhang, Dalton Trans. 2012, 41, 1457.
22. N. Jung, S. Bräse, Angew. Chem. 2012, 124, 5632
23. Angew. Chem. Int. Ed. 2012, 51, 5538.
24. S. Fantauzzi, E. Gallo, A. Caselli, F. Ragaini, P. Macchi, N. Casati, S. Cenini, Organometallics 2005, 24, 4710
25. S. Fantauzzi, E. Gallo, A. Caselli, C. Piangiolino, F. Ragaini, S. Cenini, Eur. J. Org. Chem. 2007, 6053
26. A. Caselli, E. Gallo, S. Fantauzzi, S. Morlacchi, F. Ragaini, S. Cenini, Eur. J. Inorg. Chem. 2008, 3009
27. Y. Liu, C.-M. Che, Chem. Eur. J. 2010, 16, 10494
28. S. A. Cramer, D. M. Jenkins, J. Am. Chem. Soc. 2011, 133, 19342
29. D. M. Jenkins, Synlett 2012, 1267.
30. M. Sasaki, S. Dalili, A. K. Yudin, J. Org. Chem. 2003, 68, 2045
31. D. A. Alonso, P. G. Andersson, J. Org. Chem. 1998, 63, 9455
32. S. C. Bergmeier, P. P. Seth, Tetrahedron Lett. 1999, 40, 6181.
33. R. A. Abramovitch, S. R. Challand, Y. Yamada, J. Org. Chem. 1975, 40, 1541
34. J. F. W. Keana, S. X. Cai, J. Org. Chem. 1990, 55, 3640
35. N. Soundararajan, M. S. Platz, J. Org. Chem. 1990, 55, 2034
36. K. G. Pinney, J. A. Katzenellenbogen, J. Org. Chem. 1991, 56, 3125
37. M. Yan, S. X. Cai, J. F. W. Keana, J. Org. Chem. 1994, 59, 5951.
38. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320
39. H. Amii, K. Uneyama, Chem. Rev. 2009, 109, 2119
40. K. C. K. Swamy, N. N. B. Kumar, E. Balaraman, K. V. P. P. Kumar, Chem. Rev. 2009, 109, 2551
41. D. Antonow, D. E. Thurston, Chem. Rev. 2011, 111, 2815
42. J. R. Barrio, N. Satyamurthy, S.-C. Huang, A. Petrič, G. W. Small, V. Kepe, Acc. Chem. Res. 2009, 42, 842
43. S. M. Ametamey, M. Honer, P. A. Schubiger, Chem. Rev. 2008, 108, 1501.
44. A. Caselli, E. Gallo, F. Ragaini, F. Ricatto, G. Abbiati, S. Cenini, Inorg. Chim. Acta 2006, 359, 2924.
45. A. I. Olivos Suarez, H. Jiang, X. P. Zhang, B. de Bruin, Dalton Trans. 2011, 40, 5697
46. K. H. Hopmann, A. Ghosh, ACS Catal. 2011, 1, 597; for related DFT studies on the radical mechanism of [Co(Por)]-catalyzed C-H amination, see
47. III-carbene radical intermediates, see
48. W. I. Dzik, X. Xu, X. P. Zhang, J. N. H. Reek, B. de Bruin, J. Am. Chem. Soc. 2010, 132, 10891
49. J. L. Belof, C. R. Cioce, X. Xu, X. P. Zhang, B. Space, H. L. Woodcock, Organometallics 2011, 30, 2739
50. H. Lu, W. I. Dzik, X. Xu, L. Wojtas, B. de Bruin, X. P. Zhang, J. Am. Chem. Soc. 2011, 133, 8518.
51. J. V. Ruppel, J. E. Jones, C. A. Huff, R. M. Kamble, Y. Chen, X. P. Zhang, Org. Lett. 2008, 10, 1995.
52. H. Lu, H. Jiang, L. Wojtas, X. P. Zhang, Angew. Chem. 2010, 122, 10390
53. Angew. Chem. Int. Ed. 2010, 49, 10192.
54. I. Alkorta, I. Rozas, J. Elguero, J. Fluorine Chem. 2000, 101, 233
55. J. A. K. Howard, V. J. Hoy, D. O'Hagan, G. T. Smith, Tetrahedron 1996, 52, 12613
56. H.-J. Schneider, Chem. Sci. 2012, 3, 1381.
57. Y. Chen, K. B. Fields, X. P. Zhang, J. Am. Chem. Soc. 2004, 126, 14718.
58. X. Xu, H. Lu, J. V. Ruppel, X. Cui, S. Lopez de Mesa, L. Wojtas, X. P. Zhang, J. Am. Chem. Soc. 2011, 133, 15292.
59. NAr reactions, see related references
60. M. Bella, S. Kobbelgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 3670
61. L. Qin, C. Sheridan, J. Gao, Org. Lett. 2012, 14, 528
62. A. Rolfe, T. B. Samarakoon, P. R. Hanson, Org. Lett. 2010, 12, 1216.