Nickel-catalyzed intramolecular [3 + 2 + 2] cycloadditions of alkylidenecyclopropanes. A straightforward entry to fused 6,7,5-tricyclic systems

Organic Letters

Volumn 16, Issue 19, 2014, Pages 5008-5011

  Saya, Lucía ^a   Fernández, Israel ^b   López, Fernando ^a,c   Mascareñas, José L ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^c INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; CYCLOPROPANE DERIVATIVE; FUSED HETEROCYCLIC RINGS; NICKEL;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; CYCLOADDITION; STEREOISOMERISM; SYNTHESIS;

ALKENES; ALKYNES; CATALYSIS; CYCLIZATION; CYCLOADDITION REACTION; CYCLOPROPANES; HETEROCYCLIC COMPOUNDS, 3-RING; MOLECULAR STRUCTURE; NICKEL; STEREOISOMERISM;

EID: 84907702438     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502288x     Document Type: Article

References (37)

1. Wender, P. A.; Miller, B. L. Nature 2009, 264, 197
2. Inglesby, P. A.; Evans, P. A. Chem. Soc. Rev. 2010, 39, 2791
3. Balme, G.; Bouyssi, G.; Monteiro, N. In Multicomponent Reactions; Zhu, J.; Bienaymé, H., Eds.; Wiley-VCH: Weinheim, 2005; pp 224-276.
4. Heller, B.; Hapke, M. Chem. Soc. Rev. 2007, 36, 1085
5. Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901
6. Montgomery, J. Acc. Chem. Res. 2000, 33, 467
7. Kumar, P.; Louie, J. Nickel-Mediated Cycloaddition, [2 + 2 + 2] and [2 + 2 + 1] Cycloaddition. In Transition-Metal-Mediated Aromatic Ring Construction; Tanaka, K., Ed.; John Wiley & Sons Ltd.: Chichester, 2012.
8. Komagawa, S.; Wang, C.; Morokuma, K.; Saito, S.; Uchiyama, M. J. Am. Chem. Soc. 2013, 135, 14508
9. Saito, S.; Komagawa, S.; Azumaya, I.; Masuda, M. J. Org. Chem. 2007, 72, 9114
10. Maeda, K.; Saito, S. Tetrahedron Lett. 2007, 48, 3173
11. Komagawa, S.; Saito, S. Angew. Chem., Int. Ed. 2006, 45, 2446
12. Zhao, L.; de Meijere, A. Adv. Synth. Catal. 2006, 348, 2484
13. Saya, L.; Bhargava, G.; Navarro, M. A.; Gulías, M.; López, F.; Fernández, I.; Castedo, L.; Mascareñas, J. L. Angew. Chem., Int. Ed. 2010, 49, 9886
14. Kumar, P.; Zhang, K.; Louie, J. Angew. Chem., Int. Ed. 2012, 51, 8602
15. Kumar, P.; Troast, D. M.; Cella, R.; Louie, J. J. Am. Chem. Soc. 2011, 133, 7719
16. Saito, S.; Maeda, K.; Yamasaki, R.; Kitamura, T.; Nakagawa, M.; Kato, K.; Azumaya, I.; Masu, H. Angew. Chem., Int. Ed. 2010, 49, 1830
17. Wender, P. A.; Christy, J. P.; Lesser, A. B.; Gieseler, M. T. Angew. Chem., Int. Ed. 2009, 48, 7687
18. Rigby, J. H. Stud. Nat. Prod. Chem. 1993, 12, 233
19. Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897
20. Ovaska, T. V.; Reisman, S. E.; Flynn, M. A. Org. Lett. 2001, 3, 115
21. Paquette, L.; Gallou, F.; Zhao, Z.; Young, D. G.; Liu, J.; Yang, J.; Friedrich, D. J. Am. Chem. Soc. 2000, 122, 9610
22. Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976
23. Jackson, S. R.; Johnson, M. G.; Mikami, M.; Shiokawa, S.; Carreira, E. M. Angew. Chem., Int. Ed. 2001, 40, 2694
24. Bhargava, G.; Trillo, B.; Araya, M.; López, F.; Castedo, L.; Mascareñas, J. L. Chem. Commun. 2010, 46, 270
25. Evans, P. A.; Inglesby, P. A. J. Am. Chem. Soc. 2008, 130, 12838
26. Evans, P. A.; Inglesby, P. A.; Kilbride, K. Org. Lett. 2013, 15, 1798
27. Araya, M.; Gulías, M.; Fernández, I.; Bhargava, G.; Castedo, L.; Mascareñas, J. L.; López, F. Chem. - Eur. J. 2014, 20, 10255
28. Battiste, M. A.; Pelphrey, P. M.; Wright, D. L. Chem. - Eur. J. 2006, 12, 3438
29. Jiao, L.; Lin, M.; Yu, Z.-X. Chem. Commun. 2010, 46, 1059
30. Jiao, L.; Lin, M.; Yu, Z.-X. J. Am. Chem. Soc. 2011, 133, 447
31. Lin, M.; Kang, G.-Y.; Guo, Y.-A.; Yu, Z.-X. J. Am. Chem. Soc. 2012, 134, 398
32. Hong, X.; Liu, P.; Houk, K. N. J. Am. Chem. Soc. 2013, 135, 1456
33. Delgado, A.; Rodríguez, J. R.; Castedo, L.; Mascareñas, J. L. J. Am. Chem. Soc. 2003, 125, 9282
34. Durán, J.; Gulias, M.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2005, 7, 5693
35. Trillo, B.; Gulias, M.; López, F.; Castedo, L.; Mascareñas, J. L. Adv. Synth. Catal. 2006, 348, 2381
36. Related [2 + 2 + 2 + 2] cycloadditions of non-symmetrical bisdiynes had been previously described by Wender et al. using [(dme)NiBr2]/Zn as catalyst, although the reported regioselectivity was complementary to that of 4i and 4j; see ref 6d and Wender, P. A.; Christy, J. P. J. Am. Chem. Soc. 2007, 129, 13402
37. 1,6-Enynes have also been shown to participate in Ni-catalyzed [2 + 2 + 2 + 2] cycloadditions; see: Chai, Z.; Wang, H.-F.; Zhao, G. Synlett 2009, 1785