Stereoselective nitration of olefins with tBuONO and TEMPO: Direct access to nitroolefins under metal-free conditions

Organic Letters

Volumn 15, Issue 13, 2013, Pages 3384-3387

  Maity, Soham ^a   Naveen, Togati ^a   Sharma, Upendra ^a   Maiti, Debabrata ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; HETEROCYCLIC COMPOUND; METAL; NITRO DERIVATIVE; NITROSO DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; CATALYSIS; HETEROCYCLIC COMPOUNDS; METALS; NITRO COMPOUNDS; NITROSO COMPOUNDS; STEREOISOMERISM;

EID: 84879998422     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401426p     Document Type: Article

References (56)

1. Barrett, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 86, 751
2. Talalay, P.; Delong, M. J.; Prochaska, H. J. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8261
3. Alston, T. A.; Porter, D. J. T.; Bright, H. J. Bioorg. Chem. 1985, 13, 375
4. Cheng, P.; Jiang, Z. Y.; Wang, R. R.; Zhang, X. M.; Wang, Q.; Zheng, Y. T.; Zhou, J.; Chen, J. J. Bioorg. Med. Chem. Lett. 2007, 17, 4476
5. Kaap, S.; Quentin, I.; Tamiru, D.; Shaheen, M.; Eger, K.; Steinfelder, H. J. Biochem. Pharmacol. 2003, 65, 603
6. Kim, J. H.; Kim, J. H.; Lee, G. E.; Lee, J. E.; Chung, I. K. Mol. Pharmacol. 2003, 63, 1117
7. Uehara, H.; Imashiro, R.; Hernandez-Torres, G.; Barbas, C. F. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20672
8. Meah, Y.; Massey, V. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 10733
9. Sakai, K.; Nakazawa, A.; Kondo, K.; Ohta, H. Agric. Biol. Chem. 1985, 49, 2331
10. Reddy, M. A.; Jain, N.; Yada, D.; Kishore, C.; Reddy, V. J.; Reddy, P. S.; Addlagatta, A.; Kalivendi, S. V.; Sreedhar, B. J. Med. Chem. 2011, 54, 6751
11. Lu, L. Q.; Chen, J. R.; Xiao, W. J. Acc. Chem. Res. 2012, 45, 1278
12. Ballini, R.; Bosica, G. J. Org. Chem. 1997, 62, 425
13. Fioravanti, S.; Pellacani, L.; Tardella, P. A.; Vergari, M. C. Org. Lett. 2008, 10, 1449
14. Kancharla, P. K.; Reddy, Y. S.; Dharuman, S.; Vankar, Y. D. J. Org. Chem. 2011, 76, 5832
15. Jovel, I.; Prateeptongkum, S.; Jackstell, R.; Vogl, N.; Weckbecker, C.; Beller, M. Adv. Synth. Catal. 2008, 350, 2493
16. Campos, P. J.; Garcia, B.; Rodriguez, M. A. Tetrahedron Lett. 2000, 41, 979
17. Suzuki, H.; Mori, T. J. Org. Chem. 1997, 62, 6498
18. Mukaiyama, T.; Hata, E.; Yamada, T. Chem. Lett. 1995, 505
19. Sy, W. W.; By, A. W. Tetrahedron Lett. 1985, 26, 1193
20. Varma, R. S.; Naicker, K. P.; Liesen, P. J. Tetrahedron Lett. 1998, 39, 3977
21. Hata, E.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 3629
22. Ranganathan, S.; Kar, S. K. J. Org. Chem. 1970, 35, 3962
23. Tinsley, S. W. J. Org. Chem. 1961, 26, 4723
24. Corey, E. J.; Estreicher, H. J. Am. Chem. Soc. 1978, 100, 6294
25. Jew, S. S.; Kim, H. D.; Cho, Y. S.; Cook, C. H. Chem. Lett. 1986, 1747
26. Zhu, C.; Li, G. Q.; Ess, D. H.; Falck, J. R.; Kurti, L. J. Am. Chem. Soc. 2012, 134, 18253
27. O'Brien, J. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2011, 133, 7712
28. Kantak, A. A.; Potavathri, S.; Barham, R. A.; Romano, K. M.; DeBoef, B. J. Am. Chem. Soc. 2011, 133, 19960
29. Cho, S. H.; Yoon, J.; Chang, S. J. Am. Chem. Soc. 2011, 133, 5996
30. Pelletier, G.; Bechara, W. S.; Charette, A. B. J. Am. Chem. Soc. 2010, 132, 12817
31. Bu, X. D.; Koide, K.; Carder, E. J.; Welch, C. J. Org. Process Res. Dev. 2013, 17, 108
32. Hermann, J. C.; Chen, Y. S.; Wartchow, C.; Menke, J.; Gao, L.; Gleason, S. K.; Haynes, N. E.; Scott, N.; Petersen, A.; Gabriel, S.; Vu, B.; George, K. M.; Narayanan, A.; Li, S. H.; Qian, H.; Beatini, N.; Niu, L. H.; Gan, Q. F. ACS Med. Chem. Lett. 2013, 4, 197
33. Qiu, F. H.; Norwood, D. L. J. Liq. Chromatogr. Relat. Technol. 2007, 30, 877
34. Garrett, C. E.; Prasad, K. Adv. Synth. Catal. 2004, 346, 889
35. Welch, C. J.; Albaneze-Walker, J.; Leonard, W. R.; Biba, M.; DaSilva, J.; Henderson, D.; Laing, B.; Mathre, D. J.; Spencer, S.; Bu, X. D.; Wang, T. B. Org. Process Res. Dev. 2005, 9, 198
36. Manna, S.; Maity, S.; Rana, S.; Agasti, S.; Maiti, D. Org. Lett. 2012, 14, 1736
37. Maity, S.; Manna, S.; Rana, S.; Naveen, T.; Mallick, A.; Maiti, D. J. Am. Chem. Soc. 2013, 135, 3355
38. Selective nitration of olefin can also be achieved with iron nitrate/TEMPO: Naveen, T.; Maity, S.; Sharma, U.; Maiti, D. J. Org. Chem. 2013, 10.1021/jo400598p
39. Nitroolefins through decarboxylative nitration of aromatic acrylic acid derivatives: Manna, S.; Jana, S.; Saboo, T.; Maji, A.; Maiti, D. Chem. Commun. 2013, 49, 5286
40. Culotta, E.; Koshland, D. E. Science 1992, 258, 1862
41. Ballini, R.; Araujo, N.; Gil, M. a. V.; Roman, E.; Serrano, J. A. Chem. Rev. 2013, 113, 3493
42. Experimental details of the structure determination can be found in the Supporting Information. CCDC-932098 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data- request/cif.
43. Liu, Y. Synlett 2011, 2011, 1184
44. Koley, D.; Colon, O. C.; Savinov, S. N. Org. Lett. 2009, 11, 4172
45. Taniguchi, T.; Yajima, A.; Ishibashi, H. Adv. Synth. Catal. 2011, 353, 2643
46. Kilpatrick, B.; Heller, M.; Arns, S. Chem. Commun. 2013, 49, 514
47. Taniguchi, T.; Sugiura, Y.; Hatta, T.; Yajima, A.; Ishibashi, H. Chem. Commun. 2013, 49, 2198
48. Wu, X. F.; Schranck, J.; Neumann, H.; Beller, M. Chem. Commun. 2011, 47, 12462
49. Galliker, B.; Kissner, R.; Nauser, T.; Koppenol, W. H. Chem.-Eur. J. 2009, 15, 6161
50. Vogler, T.; Studer, A. Synthesis-Stuttgart 2008, 1979
51. Tebben, L.; Studer, A. Angew. Chem., Int. Ed. 2011, 50, 5034
52. He, Z. H.; Kirchberg, S.; Frohlich, R.; Studer, A. Angew. Chem., Int. Ed. 2012, 51, 3699
53. Li, Y.; Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8221
54. Hartmann, M.; Li, Y.; Studer, A. J. Am. Chem. Soc. 2012, 134, 16516
55. Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 16901
56. Hoover, J. M.; Ryland, B. L.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 2357 Technology