Highly regio- and stereoselective nitro-oxoamination of mono-substituted allenes

Chemical Communications

Volumn 50, Issue 97, 2014, Pages 15333-15336

  Xue, Can ^a   Fu, Chunling ^a   Ma, Shengming ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; ALKENE; AMINE OXIDE; SILVER NITRATE; TEMPO;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; NITRO OXOAMINATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; AMINATION; CHEMISTRY; STEREOISOMERISM;

ALKENES; AMINATION; CYCLIC N-OXIDES; SILVER NITRATE; STEREOISOMERISM;

EID: 84911454694     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc05743k     Document Type: Article

References (39)

1. E. J. Corey, H. Estreicher, J. Am. Chem. Soc., 1978, 100:6294
2. A. G. M. Barrett, G. G. Graboski, Chem. Rev., 1986, 86:751
3. H. Feuer and T. Nielsen, Nitro Compounds: Recent Advances in Synthesis and Chemistry, VCH, New York, 1990
4. S. E. Denmark, A. Thorarensen, Chem. Rev., 1996, 96:137
5. N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001
6. R. Ballini, M. Petrini, ARKIVOC, 2009, 195
7. D. Basavaiah, B. S. Reddy, S. S. Badsara, Chem. Rev., 2010, 110:5447
8. L.-Q. Lu, J.-R. Chen, W.-J. Xiao, Acc. Chem. Res., 2012, 45:1278
9. Y. Meah, V. Massey, Proc. Natl. Acad. Sci. U. S. A., 2000, 97:10733
10. S. Kaap, I. Quentin, D. Tamiru, M. Shaheen, K. Eger, H. J. Steinfelder, Biochem. Pharmacol., 2003, 65:603
11. J. H. Kim, J. H. Kim, G. E. Lee, J. E. Lee, I. K. Chung, Mol. Pharmacol., 2003, 63:1117
12. P. Cheng, Z. Y. Jiang, R. R. Wang, X. M. Zhang, Q. Wang, Y. T. Zheng, J. Zhou, J. J. Chen, Bioorg. Med. Chem. Lett., 2007, 17:4476
13. M. A. Reddy, N. Jain, D. Yada, C. Kishore, V. J. Reddy, P. S. Reddy, A. Addlagatta, S. V. Kalivendi, B. Sreedhar, J. Med. Chem., 2011, 54:6751
14. G. Yan, A. J. Borah, L. Wang, Org. Biomol. Chem., 2014, 12:6049
15. L. Henry, C. R. Hebd. Seances Acad. Sci., 1895, 120:1265
16. F. A. Luzzio, Tetrahedron, 2001, 57:915
17. J. Boruwa, N. Gogoi, P. P. Saikia, N. C. Barua, Tetrahedron: Asymmetry, 2006, 17:3315
18. C. Palomo, M. Oiarbide, A. Laso, Eur. J. Org. Chem., 2007, 2561
19. S. Fioravanti, L. Pellacani, P. A. Tardella, M. C. Vergari, Org. Lett., 2008, 10:1449
20. S. R. Waldman, A. P. Monte, A. Bracey, D. E. Nichols, Tetrahedron Lett., 1996, 37:7889
21. S. Maity, S. Manna, S. Rana, T. Naveen, A. Mallick, D. Maiti, J. Am. Chem. Soc., 2013, 135:3355
22. S. Maity, T. Naveen, U. Sharma, D. Maiti, Synlett, 2014, 603
23. J. R. Hwu, K.-L. Chen, S. Ananthan, H. V. Patel, Organometallics, 1996, 15:499
24. A. V. Stepanov, V. V. Veselovsky, Russ. Chem. Rev., 2003, 72:327
25. K. Jayakanthan, K. P. Madhusudanan, Y. D. Vankar, Tetrahedron, 2004, 60:397
26. E. Lewandowska, Tetrahedron, 2006, 62:4879
27. T. Taniguchi, T. Fujii, H. Ishibashi, J. Org. Chem., 2010, 75:8126
28. T. Naveen, S. Maity, U. Sharma, D. Maiti, J. Org. Chem., 2013, 78:5949
29. S. Manna, S. Jana, T. Saboo, A. Maji, D. Maiti, Chem. Commun., 2013, 49:5286
30. S. Maity, T. Naveen, U. Sharma, D. Maiti, Org. Lett., 2013, 15:3384
31. I. Jovel, S. Prateeptongkum, R. Jackstell, N. Vogl, C. Weckbecker, M. Beller, Adv. Synth. Catal., 2008, 350:2493
32. L. Tebben, A. Studer, Angew. Chem., Int. Ed., 2011, 50:5034
33. J.-Q. Kuang, S.-M. Ma, J. Org. Chem., 2009, 74:1763
34. F. Pan, C.-L. Fu, S.-M. Ma, Chin. J. Org. Chem., 2004, 24:1168
35. V. K. Wieser, A. Berndt, Angew. Chem., Int. Ed. Engl., 1975, 14:69
36. V. R. Sabbasani, D. Lee, Org. Lett., 2013, 15:3954
37. S. P. Waters, M. W. Fennie, M. C. Kozlowski, Org. Lett., 2006, 8:3243
38. N. Kise, S. Isemoto, T. Sakurai, J. Org. Chem., 2011, 76:9856
39. Z.-G. Chen, Y. Wang, J.-F. Wei, P.-F. Zhao, X.-Y. Shi, J. Org. Chem., 2010, 75:2085