Indium-catalyzed homo-nazarov cyclizations of alkenyl cyclopropyl ketones

Organic Letters

Volumn 12, Issue 24, 2010, Pages 5684-5687

  Patil, Dadasaheb V ^a   Phun, Lien H ^a   France, Stefan ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78650336360     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102497w     Document Type: Article

References (29)

1. Reissig, H.-U. In Small Ring Compounds in Organic Synthesis III; Meijere, A. de, Ed.; Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, Germany, 1988; Vol. 144, p 1.
2. Hudlicky, T. Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 899.
3. Rubin, M.; Rubia, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117
4. Yu, M.; Pagenkopf, B. L. Tetrahedron 2005, 61, 321
5. Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151
6. For recent representative examples, see Carson, C. A.; Young, I. S.; Kerr, M. A. Synthesis 2008, 485
7. Ivanova, O. A.; Budynina, E. M.; Grishin, Y. K.; Trushkov, I. V.; Verteletskii, P. V. Angew. Chem. 2008, 120, 1123
8. Pohlhaus, P. D.; Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 16014
9. Sugita, Y.; Yamadoi, S.; Hosoya, H.; Yokoe, I. Chem. Pharm. Bull. 2001, 49, 657
10. For reviews, see Nakanishi, W.; West, F. G. Curr. Opin. Drug Discovery Dev. 2009, 12, 732
11. Tius, M. A. Eur. J. Org. Chem. 2005, 2193
12. Frontier, A. J.; Collison, C Tetrahedron 2005, 61, 7577
13. Pellissier, H. Tetrahedron 2005, 61, 6479
14. Murphy, W. S.; Wattansin, S. Tetrahedron Lett. 1980, 21, 1887
15. Murphy, W. S.; Wattansin, S. J. Chem. Soc., Perkins Trans. 1 1981, 2920
16. Murphy, W. S.; Wattanasin, S. J. Chem. Soc., Perkin Trans. 1 1982, 1029
17. Yadav, V. K.; Kumar, N. V. Chem. Commun. 2008, 3774
18. Tsuge, O.; Kanemasa, S.; Otsuka, T.; Suzuki, T. Bull. Chem. Soc. Jpn. 1988, 61, 2897
19. De Simone, F.; Andres, J.; Torosantucci, R.; Waser, J. Org. Lett. 2009, 11, 1023
20. He, W.; Herrick, I. R.; Atesin, T. A.; Caruana, P. A.; Kellenberger, C. A.; Frontier, A. J. J. Am. Chem. Soc. 2008, 130, 1003
21. Pohlhaus, P. D.; Sanders, S. D.; Parsons, A. T.; Li, W.; Johnson, J. S. J. Am. Chem. Soc. 2008, 130, 8642
22. This hypothesis was confirmed later when no desired cyclizations were observed with substrates bearing an -hydrogen.
23. Marcoux, D.; Charette, A. B. Angew. Chem., Int. Ed. 2008, 47, 10155
24. For recent reviews of In(III) catalysis, see Ghosh, R.; Maiti, S. J. Mol. Catal. A: Chem. 2007, 264, 1
25. Frost, C. G.; Hartley, J. P. Mini-Rev. Org. Chem. 2004, 1, 1-7
26. See Supporting Information.
27. MMFF calculations were run using Trident software available from Wavefunction, Inc.
28. Cabrera, S.; Alemán, J.; Bolze, P.; Bertelsen, S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2008, 47, 121-125
29. Krapcho, A. P.; Jahngen, E. G. E.; Lovey, A. J.; Short, F. W. Tetrahedron Lett. 1974, 15, 1091