Solvent-free, ruthenium-catalyzed, regioselective ring-opening of epoxides, an efficient route to various 3-alkylated indoles

Tetrahedron Letters

Volumn 49, Issue 9, 2008, Pages 1450-1454

  Tabatabaeian, K ^a   Mamaghani, M ^a   Mahmoodi, N O ^a   Khorshidi, A ^a  

^a UNIVERSITY OF GUILAN   (Iran)

Author keywords

Epoxides; Indoles; Ring opening; Ruthenium

Indexed keywords

ALKYL GROUP; EPOXIDE; INDOLE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RUTHENIUM; SOLVENT;

ARTICLE; CATALYSIS; CATALYST; FRIEDEL CRAFTS REACTION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; RING OPENING; STEREOCHEMISTRY;

EID: 38649098179     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.001     Document Type: Article

References (24)

1. Masters C. Homogeneous Transition Metal Catalysis-A Gentle Art (1981), Chapman and Hall Ltd
2. Murahashi S.-I. Ruthenium in Organic Synthesis (2004), Wiley-VCH, New York
3. Bruneau C., and Dixneuf P.H. Ruthenium Catalysts and Fine Chemistry (2004), Springer
4. Murai S. Activation of Unreactive Bonds and Organic Synthesis (1999), Springer
5. Murahashi S.-I., Naota T., Taki H., Mizuno M., Takaya H., Komiya S., Mizuho Y., Oyasato N., Harioka M., Hirano M., and Fukuoka A. J. Am. Chem. Soc. 117 (1995) 12436
6. Zhang H., Zhang Y., Liu L., Xu H., and Wang Y. Synthesis (2005) 2129
7. Kobayashi S., Kakumoto K., and Sugiura M. Org. Lett. 4 (2002) 1319
8. Iranpoor N., and Kazemi F. Tetrahedron 54 (1998) 9475
9. Komiya N., Noji S., and Murahashi S.-I. Chem. Commun. (2001) 65
10. Murahashi S.-I., Komiya N., Terai H., and Nakae T. J. Am. Chem. Soc. 125 (2003) 15312
11. Gilchrist T.L. Heterocyclic Chemistry (1997), Academic Press, London p 231
12. Humphrey G.R., and Kuethe J.T. Chem. Rev. 106 (2006) 2875
13. Zhang H.-C., Ye H., Moretto A.F., Brumfield K.K., and Maryanoff B.E. Org. Lett. 2 (2000) 89
14. Jung M.E., and Slowinsky F. Tetrahedron Lett. 42 (2001) 6835
15. Walsh T., Toupence R.B., Ujjainwalla F., Young J.R., and Goulet M.T. Tetrahedron 57 (2001) 5233
16. Dirlam J.P., Clark D.A., and Hecker S.J. J. Org. Chem. 51 (1986) 4920
17. Tanis S.P., and Raggon J.W. J. Org. Chem. 52 (1987) 819
18. Kotsuki H., Hayashida K., Shimanouchi T., and Nishizawa H. J. Org. Chem. 61 (1996) 984
19. Kotsuki H., Teraguchi M., Shimomoto N., and Ochi M. Tetrahedron Lett. 37 (1996) 3727
20. Kantam M.L., Laha S., Yadav J., and Sreedhar B. Tetrahedron Lett. 47 (2006) 6213
21. Bandgar B.P., and Patil A.V. Tetrahedron Lett. 48 (2007) 173
22. Tabatabaeian K., Mamaghani M., Mahmoodi N.O., and Khorshidi A. Can. J. Chem. 84 (2006) 1541
23. Tabatabaeian K., Mamaghani M., Mahmoodi N.O., and Khorshidi A. J. Mol. Catal. A 270 (2007) 112
24. Tabatabaeian K., Mamaghani M., Mahmoodi N.O., and Khorshidi A. Catal. Commun. 9 (2008) 416