Stereoselective [3+2] Carbocyclization of Indole-Derived Imines and Electron-Rich Alkenes: A Divergent Synthesis of Cyclopenta[b]indole or Tetrahydroquinoline Derivatives

Chemistry - A European Journal

Volumn 21, Issue 47, 2015, Pages 16769-16774

  Galván, Alicia ^a   Calleja, Jonás ^a   González Pérez, Adán B ^b   Álvarez, Rosana ^b   De Lera, Angel R ^b   Fañanás, Francisco J ^a   Rodríguez, Félix ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSITY OF VIGO   (Spain)

Author keywords

acid catalysis; divergent synthesis; heterocycles; indoles; synthetic methods

Indexed keywords

HYDROCARBONS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

ACID CATALYSIS; DIVERGENT SYNTHESIS; HETEROCYCLES; INDOLES; SYNTHETIC METHODS;

POLYCYCLIC AROMATIC HYDROCARBONS;

EID: 84946431068     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201503044     Document Type: Article

References (39)

1. L. S. Povarov, Russ. Chem. Rev. 1967, 36, 656-670; For excellent reviews, see:
2. V. V. Kouznetsov, Tetrahedron 2009, 65, 2721-2750;
3. M. Fochi, L. Caruana, L. Bernardi, Synthesis 2013, 46, 135-157.
4. For a recent experimental and computational work from our laboratories on the Povarov reaction, see:, J. Calleja, A. B. González-Pérez, A. R. de Lera, R. Álvarez, F. J. Fañanás, F. Rodríguez, Chem. Sci. 2014, 5, 996-1007.
5. O. Jiménez, G. de La Rosa, R. Lavilla, Angew. Chem. Int. Ed. 2005, 44, 6521-6525;
6. Angew. Chem. 2005, 117, 6679-6683;
7. G. Bergonzini, L. Gramigna, A. Mazzanti, M. Fochi, L. Bernardi, A. Ricci, Chem. Commun. 2010, 46, 327-329;
8. L. Cala, A. Mendoza, F. J. Fañanás, F. Rodríguez, Chem. Commun. 2013, 49, 2715-2717.
9. Indolyl-substituted tetrahydroquinoline derivatives have shown effective antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). See:, M. Z. Hoemann, R. L. Xie, R. F. Rossi, S. Meyer, A. Sidhu, G. D. Cuny, J. R. Hauske, Bioorg. Med. Chem. Lett. 2002, 12, 129-132.
10. Y. Ouyang, K. Koike, T. Ohmoto, Phytochemistry 1994, 37, 575-578;
11. J. P. Springer, J. Clardy, Tetrahedron Lett. 1980, 21, 231-234;
12. Y.-C. Kong, K.-F. Cheng, R. C. Cambie, P. G. Waterman, J. Chem. Soc. Chem. Commun. 1985, 47-48;
13. A. Park, R. E. Moore, G. M. L. Patterson, Tetrahedron Lett. 1992, 33, 3257-3260;
14. K. Stratmann, R. E. Moore, R. Bonjouklian, J. B. Deeter, G. M. L. Patterson, S. Shaffer, C. D. Smith, T. A. Smitka, J. Am. Chem. Soc. 1994, 116, 9935-9942;
15. E. Lai, I. De Lepeleire, T. M. Crumley, F. Liu, L. A. Wenning, N. Michiels, E. Vets, G. O'Neill, J. A. Wagner, K. Gottesdiener, Clin. Pharmacol. Ther. 2007, 81, 849-857;
16. C. F. Sturino, G. O'Neill, N. Lachance, M. Boyd, C. Berthelette, M. Labelle, L. Li, B. Roy, J. Scheigetz, N. Tsou, Y. Aubin, K. P. Bateman, N. Chauret, S. H. Day, J.-F. Lévesque, C. Seto, J. H. Silva, L. A. Trimble, M.-C. Carriere, D. Denis, G. Greig, S. Kargman, S. Lamontagne, M.-C. Mathieu, N. Sawyer, D. Slipetz, W. M. Abraham, T. Jones, M. McAuliffe, H. Piechuta, D. A. Nicoll-Griffith, Z. Wang, R. Zamboni, R. N. Young, K. M. Metters, J. Med. Chem. 2007, 50, 794-806;
17. H. Ratni, D. Blum-Kaelin, H. Dehmlow, P. Hartman, P. Jablonski, R. Masciadri, C. Maugeais, A. Patiny-Adam, N. Panday, M. Wright, Bioorg. Med. Chem. Lett. 2009, 19, 1654-1657.
18. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, revision A.01; Gaussian, Inc.: Wallingford, CT, 2009.
19. K. Fukui, Acc. Chem. Res. 1981, 14, 363-368;
20. C. Gonzalez, H. B. Schlegel, J. Phys. Chem. 1990, 94, 5523-5527.
21. J.-D. Chai, M. Head-Gordon, Phys. Chem. Chem. Phys. 2008, 10, 6615-6620. For an overview of dispersion-corrected DFT methods in the description of aromatic interactions, see:
22. S. Ehrlich, J. Moellmann, S. Grimme, Acc. Chem. Res. 2013, 46, 916-926.
23. Representations were created with CYLview, 1.0b; C. Y. Legault, Université de Sherbrooke, 2009 (http://www.cylview.org).
24. Dewar and co-workers first proposed the term two-stage mechanisms to define "reactions concerted but not synchronous, in which some of the changes in bonding takes place in the first half of the reaction while the rest takes place in the second half". See:, M. J. S. Dewar, S. Olivella, J. J. P. Stewart, J. Am. Chem. Soc. 1986, 108, 5771-5779. Houk and co-workers described these processes as "those in which the formation of two bonds takes place in separate, but overlapping, processes". Additionally, these authors suggested that these processes should be called "asynchronous concerted". See:
25. K. N. Houk, J. González, Y. Li, Acc. Chem. Res. 1995, 28, 81-90. Finally, Domingo proposed the term two-stage reactions for those "in which formation of the two σ-bonds takes place in a non-concerted process but in a single kinetic step". See:
26. L. R. Domingo, J. Org. Chem. 2001, 66, 3211-3214.
27. E. Clot, Eur. J. Inorg. Chem. 2009, 2319-2328.
28. J. D. Dunitz, R. Taylor, Chem. Eur. J. 1997, 3, 89-98;
29. R. S. Rathore, N. S. Karthiekeyan, Y. Alekhya, K. Sathiyanarayanan, P. G. Aravindan, J. Chem. Sci. 2011, 123, 403-409;
30. C. Bissantz, B. Kuhn, M. Stahl, J. Med. Chem. 2010, 53, 5061-5084.
31. F. M. Bickelhaupt, J. Comput. Chem. 1999, 20, 114-128;
32. J. DeChancie, O. Acevedo, J. D. Evanseck, J. Am. Chem. Soc. 2004, 126, 6043-6047.
33. J. Tomasi, M. Persico, Chem. Rev. 1994, 94, 2027-2094;
34. M. Cossi, G. Scalmani, N. Rega, V. Barone, J. Chem. Phys. 2002, 117, 43-54;
35. -1, Table 2).
36. M. Fleischmann, D. Drettwan, E. Sugiono, M. Rueping, R. M. Gschwind, Angew. Chem. Int. Ed. 2011, 50, 6364-6369;
37. Angew. Chem. 2011, 123, 6488-6493;
38. R. Appel, S. Chelli, T. Tokuyasu, K. Troshin, H. Mayr, J. Am. Chem. Soc. 2013, 135, 6579-6587;
39. D. Parmar, E. Sugiono, S. Raja, M. Rueping, Chem. Rev. 2014, 114, 9047-9153.