Functionalized 4-carboxy- and 4-keto-2,3-dihydropyrroles via Ni(II)-catalyzed nucleophilic amine ring-opening cyclizations of cyclopropanes

Journal of Organic Chemistry

Volumn 79, Issue 7, 2014, Pages 3030-3039

  Martin, M Cynthia ^a   Patil, Dadasaheb V ^a   France, Stefan ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; NICKEL;

CYCLIZATIONS; DONOR-ACCEPTORS; FUNCTIONALIZED; LEWIS ACID CATALYSTS; PRIMARY AMINES; REACTION CONDITIONS; RING OPENING; SYNTHETIC APPROACH;

PROPANE;

AMINE; CARBOXYL GROUP; CYCLOPROPANE DERIVATIVE; LEWIS ACID; NICKEL; PYRROLE DERIVATIVE;

ARTICLE; CATALYST; CYCLIZATION; CYCLOPROPANATION; NUCLEOPHILICITY; RING OPENING; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

AMINES; CATALYSIS; CYCLIZATION; CYCLOPROPANES; LEWIS ACIDS; MOLECULAR STRUCTURE; NICKEL; PYRROLES;

EID: 84898065888     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5001059     Document Type: Article

References (53)

1. Bellina, F.; Rossi, R. Tetrahedron 2006, 62, 7213
2. Donohoe, T. J.; Thomas, R. E. Chem. Rec. 2007, 7, 180
3. Smith, A. B., III; Charnley, A. K.; Hirschmann, R. Acc. Chem. Res. 2011, 44, 180
4. Ye, Z.; Shi, L.; Shao, X.; Xu, X.; Xu, Z.; Li, Z. J. Agric. Food Chem. 2013, 61, 312
5. Li, X.; Li, J. Mini-Rev. Med. Chem. 2010, 10, 794
6. Mal, D.; Shome, B.; Dinda, B. K. Heterocycl. Nat. Prod. Synth. 2011, 187
7. Stocker, B. L.; Dangerfield, E. M.; Win-Mason, A. L.; Haslett, G. W.; Timmer, M. S. M. Eur. J. Org. Chem. 2010, 1615
8. Tejero, T.; Merino, P.; Delso, I.; Sadaba, D. Targets Heterocycl. Syst. 2011, 15, 164
9. Bauer, I.; Knoelker, H.-J. Top. Curr. Chem. 2012, 309, 203
10. Biava, M.; Porretta, G. C.; Poce, G.; Battilocchio, C.; Alfonso, S.; de Logu, A.; Manetti, F.; Botta, M. ChemMedChem 2011, 6, 593
11. Clive, D. L. J.; Cheng, P. Tetrahedron 2013, 69, 5067
12. Dydio, P.; Lichosyt, D.; Jurczak, J. Chem. Soc. Rev. 2011, 40, 2971
13. Russel, J. S.; Pelkey, E. T.; Yoon-Miller, S. J. P. Prog. Heterocycl. Chem. 2011, 22, 143
14. Young, I. S.; Thornton, P. D.; Thompson, A. Nat. Prod. Rep. 2010, 27, 1801
15. Shi, Z.; Suri, M.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 4892
16. Zhu, Y.; Zhai, C.; Yue, Y.; Yang, L.; Hu, W. Chem. Commun. 2009, 1362
17. Wender, P. A.; Strand, D. J. Am. Chem. Soc. 2009, 131, 7528
18. Ma, S.; Yu, F.; Li, J.; Gao, W. Chem.-Eur. J. 2007, 13, 247
19. Zhou, X.; Zhang, H.; Yuan, J.; Mai, L.; Li, Y. Tetrahedron Lett. 2007, 48, 7236
20. Wolf, L. B.; Tjen, K. C. M. F.; Rutjes, F. P. J. T.; Hiemstra, H.; Schoemaker, H. E. Tetrahedron Lett. 1998, 39, 5081
21. Busacca, C. A.; Dong, Y. Tetrahedron Lett. 1996, 37, 3947
22. Xu, X.; Zhang, Y. Synth. Commun. 2003, 33, 1095
23. For an example of ring-closing metathesis to form 2,3-dihydropyrroles, see: Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. Org. Lett. 2001, 3, 2045
24. For an example of a Lewis acid-catalyzed synthesis, see: Fan, J.; Gao, L.; Wang, Z. Chem. Commun. 2009, 5021
25. Guo, C.; Xue, M.-X.; Zhu, M.-K.; Gong, L.-Z. Angew. Chem., Int. Ed. 2008, 47, 3414
26. Zhang, G.; Zhang, Y.; Jiang, X.; Yan, W.; Wang, R. Org. Lett. 2011, 13, 3806
27. Morin, M. S. T.; Aly, S.; Arndtsen, B. A. Chem. Commun. 2013, 49, 883
28. Knight, D. W.; Redfern, A. L.; Gilmore, J. Chem. Commun. 1998, 2207
29. Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc., Perkin Trans. 1 2002, 622
30. Ding, C.-H.; Dai, L.-X.; Hou, X.-L. Tetrahedron 2005, 61, 9586
31. Polindara-Garcia, L. A.; Miranda, L. D. Org. Lett. 2012, 14, 5408
32. Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440
33. Jacoby, D.; Celerier, J. P.; Haviari, G.; Petit, H.; Lhommet, G. Synthesis 1992, 884
34. Maruoka, H.; Okabe, F.; Yamagata, K. J. Heterocycl. Chem. 2007, 44, 201
35. Wurz, R. P.; Charette, A. B. Org. Lett. 2005, 7, 2313
36. Patil, D. V.; Phun, L. H.; France, S. Org. Lett. 2010, 12, 5684
37. Phun, L. H.; Patil, D. V.; Cavitt, M. A.; France, S. Org. Lett. 2011, 13, 1952
38. Patil, D. V.; Cavitt, M. A.; Grzybowski, P.; France, S. Chem. Commun. 2011, 47, 10278
39. Lifchits, O.; Charette, A. B. Org. Lett. 2008, 10, 2809
40. Zhou, Y.-Y.; Wang, L.-J.; Li, J.; Sun, X.-L.; Tang, Y. J. Am. Chem. Soc. 2012, 134, 9066
41. Nishimura, T.; Yasuhara, Y.; Sawano, T.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 7872
42. Sawano, T.; Ashouri, A.; Nishimura, T.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 18936
43. Silvi, M.; Chatterjee, I.; Liu, Y.; Melchiorre, P. Angew. Chem., Int. Ed. 2013, 52, 10780
44. Payette, J. N.; Honda, T.; Yoshizawa, H.; Favaloro, F. G.; Gribble, G. W. J. Org. Chem. 2006, 71, 416
45. Swaminathan, S.; John, J. P.; Ramachandran, S. Tetrahedron Lett. 1962, 3, 729
46. Barna, A. V.; Lampeka, Y. D. Theor. Exp. Chem. 2007, 43, 204
47. Beaver, M. G.; Jamison, T. F. Org. Lett. 2011, 13, 4140
48. Gao, Q.; Zheng, B.-F.; Li, J.-H.; Yang, D. Org. Lett. 2006, 7, 2185
49. Molinaro, C.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 8076
50. Funke, C.; Es-Sayed, M.; de Meijere, A. Org. Lett. 2000, 2, 4249
51. Gonzalez-Bobes, F.; Fenster, M. D. B.; Kiau, S.; Kolla, L.; Kolotuchin, S.; Soumeillant, M. Adv. Synth. Catal. 2008, 350, 813
52. Gopinath, P.; Chandrasekaran, S. J. Org. Chem. 2011, 76, 700
53. Marcoux, D.; Charette, A. B. Angew. Chem., Int. Ed. 2008, 47, 10155