Six-membered cyclic nitronates as 1,3-dipoles in formal [3 + 3]-cycloaddition with donor-acceptor cyclopropanes. synthesis of new type of bicyclic nitrosoacetals

Organic Letters

Volumn 15, Issue 2, 2013, Pages 350-353

  Gorbacheva, Evgenia O ^a,b   Tabolin, Andrey A ^a   Novikov, Roman A ^a   Khomutova, Yulia A ^a   Nelyubina, Yulia V ^c   Tomilov, Yury V ^a   Ioffe, Sema L ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b MENDELEEV UNIVERSITY OF CHEMICAL TECHNOLOGY OF RUSSIA   (Russian Federation)

^c A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84872521320     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol303292c     Document Type: Article

References (49)

1. Mel'nikov, M. Ya.; Budynina, E. M.; Ivanova, O. A.; Trushkov, I. V. Mendeleev Commun. 2011, 21, 293
2. Carson, C. A.; Kerr, M. A. Chem. Soc. Rev. 2009, 38, 3051
3. Yu, M.; Pagenkopf, B. L. Tetrahedron 2005, 61, 321
4. Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151
5. Zhou, Y.-Y.; Wang, L.-J.; Li, J.; Sun, X.-L.; Tang, Y. J. Am. Chem. Soc. 2012, 134, 9066
6. Emmett, M. R.; Grover, H. K.; Kerr, M. A. J. Org. Chem. 2012, 77, 6634
7. Chen, G.-Q.; Tang, X.-Y.; Shi, M. Chem. Commun. 2012, 48, 2340
8. So, S. S.; Auvil, T. J.; Garza, V. J.; Mattson, A. M. Org. Lett. 2012, 14, 444
9. Chung, S. W.; Plummer, M. S.; McAllister, L. A.; Oliver, R. M., III; Abramite, J. A.; Shen, Y.; Sun, J.; Uccello, D. P.; Arcari, J. T.; Price, L. M.; Montgomery, J. I. Org. Lett. 2011, 13, 5338
10. Emmett, M. R.; Kerr, M. A. Org. Lett. 2011, 13, 4180
11. Espejo, V. R.; Li, X.-B.; Rainier, J. D. J. Am. Chem. Soc. 2010, 132, 8282
12. Sapeta, K.; Kerr, M. A. Org. Lett. 2009, 11, 2081
13. Lifchits, O.; Charette, A. B. Org. Lett. 2008, 10, 2809
14. de Nanteuil, F.; Waser, J. Angew. Chem., Int. Ed. 2011, 50, 12075
15. Fang, J.; Ren, J.; Wang, J. Tetrahedron Lett. 2008, 49, 6659
16. Qi, X.; Ready, J. M. Angew. Chem., Int. Ed. 2008, 47, 7068
17. Bajtos, B.; Yu, M.; Zhao, H.; Pagenkopf, B. L. J. Am. Chem. Soc. 2007, 129, 9631
18. Benfatti, F.; de Nanteuil, F.; Waser, J. Org. Lett. 2012, 14, 386
19. Pohlhaus, P. D.; Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 16014
20. Meyers, C.; Carreira, E. Angew. Chem., Int. Ed. 2003, 42, 694
21. Morra, N. A.; Morales, C. L.; Bajtos, B.; Wang, X.; Jang, H.; Wang, J.; Yu, M.; Pagenkopf, B. L. Adv. Synth. Catal. 2006, 348, 2385
22. Yu, M.; Pagenkopf, B. L. J. Am. Chem. Soc. 2003, 125, 8122
23. Yu, M.; Pagenkopf, B. L. Org. Lett. 2003, 5, 5099
24. Young, I. S.; Kerr, M. A. Angew. Chem., Int. Ed. 2003, 42, 3023
25. Zhang, Y.; Liu, F.; Zhang, J. Chem.-Eur. J. 2010, 16, 6146
26. Dias, D. A.; Kerr, M. A. Org. Lett. 2009, 11, 3694
27. Hu, B.; Zhu, J.; Xing, S.; Fang, J.; Du, D.; Wang, Z. Chem.-Eur. J. 2009, 15, 324
28. Ganton, M. D.; Kerr, M. A. J. Org. Chem. 2004, 69, 8554
29. Young, I. S.; Kerr, M. A. Org. Lett. 2004, 6, 139
30. Kang, Y.-B.; Sun, X.-L.; Tang, Y. Angew. Chem., Int. Ed. 2007, 46, 3918
31. Sapeta, K.; Kerr, M. A. J. Org. Chem. 2007, 72, 8597
32. Sibi, M.; Ma, Z.; Jasperse, C. P. J. Am. Chem. Soc. 2005, 127, 5764
33. Sukhorukov, A. Yu.; Dilman, A. D.; Ioffe, S. L. Khim. Get. Soed. 2012, 54
34. Engl.: Chem. Het. Comp. 2012, 48, 49.
35. Ioffe, S. L. Nitrile oxides, nitrones, and nitronates in organic synthesis, 2 nd ed.; Feuer, H., Ed.; John Wiley & Sons: Hoboken, NJ, 2008; Chapter 3, p 541.
36. Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137
37. Denmark, S. E.; Baiazitov, R. Y.; Nguyen, S. T. Tetrahedron 2009, 65, 6535
38. Denmark, S. E.; Montgomery, J. I. Angew. Chem., Int. Ed. 2005, 44, 3732
39. Denmark, S. E.; Juhl, M. Helv. Chim. Acta 2002, 85, 3712
40. Denmark, S. E.; Hurd, A. J. Org. Chem. 2000, 65, 2875
41. Denmark, S. E.; Martinborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046
42. Denmark, S. E.; Dixon, J. A. J. Org. Chem. 1998, 63, 6167
43. Righi, P.; Marotta, E.; Rosini, G. Chem.-Eur. J. 1998, 4, 2501
44. Intriguingly annelation of DAC with cyclic nitrones gave no adducts; see: Carson, C. A.; Kerr, M. A. Angew. Chem., Int. Ed. 2006, 45, 6560
45. Shitkin, V. M.; Khudak, V. I.; Chlenov, I. E.; Tartakovskii, V. A. Izv. Akad. Nauk. SSSR, Ser. Khim. 1974, 1908 (Engl.: Bull. Akad. Sci. USSR, Div. Chem. Sci. 1974, 23, 1836)
46. Shitkin, V. M.; Chlenov, I. E.; Tartakovskii, V. A. Izv. Akad. Nauk. SSSR, Ser. Khim. 1977, 211 (Engl.: Bull. Akad. Sci. USSR, Div. Chem. Sci. 1977, 26, 187)
47. Denmark, S. E.; Thorarensen, A.; Swiss, K. A. Acta Crystallogr., Sect. C 1996, C52, 2558
48. Kuster, G. J.; Kalmoua, F.; de Gelder, R.; Scheeren, H. W. Chem. Commun. 1999, 855
49. Denmark, S. E.; Baiazitov, R. Y. J. Org. Chem. 2006, 71, 593