Triflic acid-catalyzed highly stereoselective friedel-crafts aminoalkylation of indoles and pyrroles

Organic Letters

Volumn 10, Issue 5, 2008, Pages 933-935

  Abid, Mohammed ^a   Teixeira, Liliana ^a   Török, Béla ^a  

^a UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; DRUG DERIVATIVE; FLUORINATED HYDROCARBON; GLYCINE; INDOLE DERIVATIVE; MESYLIC ACID DERIVATIVE; PYRROLE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; AMINES; CATALYSIS; GLYCINE; HYDROCARBONS, FLUORINATED; INDOLES; MESYLATES; MOLECULAR STRUCTURE; PYRROLES; STEREOISOMERISM;

EID: 43549085582     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol703095d     Document Type: Article

References (31)

1. Fried, J.; Sabo, E. F. J. Am. Chem. Soc. 1954, 76, 1455.
2. Soloshonok, V. A., Ed. Enantiocontrolled Synthesis of Fluoro-organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Wiley: New York, 1999; Ramachandran, P. V., Ed. Asymmetric Fluoro-organic Chemistry, ACS Symp. Series; American Chemical Society: Washington, D.C., 2000; Hiyama, T., Ed. Organofluorine Compounds; Springer: Berlin, 2001; Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: New York, 2004; Soloshonok, V. A., Ed. Fluorine-Containing Synthons; ACS Symp. Series; American Chemical Society: Washington D.C., 2005; Prakash, G. K. S.; Beier, P. Angew. Chem., Int. Ed. 2006, 45, 2172.
3. Prakash, G. K. S.; Yudin, A. Chem. Rev. 1997, 97, 757;
4. Prakash, G. K. S.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589;
5. Török, M.; Abid, M.; Mhadgut, S. C; Török, B. Biochemistry 2006, 45, 5377.
6. Yoder, N. C; Kumar, K. Chem. Soc. Rev. 2002, 31, 335;
7. Lazzaro, F.; Crucianelli, M.; De Angelis, F.; Frigerio, M.; Malpezzi, L.; Volonterio, A.; Zanda, M. Tetrahedron: Asymmetry 2004, 75, 889;
8. Papeo, G.; Giordano, P.; Brasca, M. G.; Buzzo, F.; Caronni, D.; Ciprandi, F.; Mongelli, N.; Veronesi, M.; Vulpetti, A.; Dalvit, C. J. Am. Chem. Soc. 2007, 129, 5665.
9. Olah, G. A., Ed. Friedel-Crafts and Related Reactions; Wiley: New York, 1965; Sheldon, R. A., van Bekkum, FL, Eds. Friedel-Crafts Alkylation; Wiley-VCH: New York, 2001.
10. Johannsen, M. Chem. Commun. 1999, 2233;
11. Saaby, S.; Fang, X.; Gartherhood, N.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114;
12. Jiang, B.; Huang, Z.-G. Synthesis 2005, 2198.
13. Jensen, K. B.; Thorhauge, J.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 160;
14. Bandini, M.; Melloni, A.; Umani-Ronchi, R. Angew. Chem., Int. Ed. 2004, 43, 550;
15. Evans, D. A.; Fandric, K. A.; Song, H.-J. J. Am. Chem. Soc. 2005, 127, 8942.
16. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370;
17. Herrera, R. P.; Sgarzani, V.; Bemardi, L.; Ricci, A. Angew. Chem., Int. Ed. 2005, 44, 6576;
18. Wang, Y.-Q.; Song, I; Hong, R.; Li, H.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156;
19. Rang. Q.; Zhao. Z.-A.; You, S.-L. J. Am. Chem. Soc. 2007, 129, 1484.
20. Terada, M.; Sorimaclii, K. J. Am. Chem. Soc. 2007, 129, 292;
21. Kang, Q.; Zhao, Z.-A.; You. S.-L. J. Am. Chem. Soc. 2007, 129, 1484;
22. Jia, Y.-X.; Zhong, J.; Zhu, S.-F.; Zhang, C.-M.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2007, 46, 5565.
23. Onys'ko, P. P.; Rassukanaya, Yu. V.; Sinitsa, A. D. Z. Obsch. Knim. 2002, 72, 1699;
24. Soloshonok, V. A.; Kukhar, V. P. Z. Org. Khim. 1990. 26, 419;
25. Osipov, S. N.; Chkanikov, N. D.; Shklyaev. Yu. V.; Kolomiets, A. F.; Fokin, A. V. Izv. Akad. Nauk, Ser. Khim. 1989, 2131;
26. Osipov, S. N.; Chkanikov, N. D.; Kolomiets, A. F.; Fokin, A. V. Izv. Akad. Nauk, Ser. Khim. 1986, 1384.
27. Török, B.; Abid. M.; London, G.; Esquibel, I; Török. M.; Mhadgut. S. C; Yan, P.; Prakash, G. K. S. Angew. Chem., Int. Ed. 2005, 44, 3086.
28. Olali, G. A.; Prakash. G. K. S.; Sommer, J. Superacids; Wilev: New York, 1985.
29. Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1977, 42, 2436.
30. Bisel. P.; Breifling. E.; Frahm, A. W. Eur. J. Org. Chem. 1998, 729.
31. Török, B.; Prakash, G. K. S. Adv. Synth. Catal. 2003, 345, 165.