Fast and highly regioselective allylation of indole and pyrrole compounds by allyl alcohols using Ru-sulfonate catalysts

Journal of the American Chemical Society

Volumn 130, Issue 35, 2008, Pages 11604-11605

  Zaitsev, Alexey B ^a   Gruber, Stefan ^a   Plüss, Pascal A ^a   Pregosin, Paul S ^a   Veiros, Luis F ^b   Wörle, Michael ^a  

^a LABORATORY OF INORGANIC CHEMISTRY   (Switzerland)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; INDOLE DERIVATIVE; PYRROLE DERIVATIVE; RUTHENIUM; SULFONIC ACID DERIVATIVE;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE;

ALLYL COMPOUNDS; CATALYSIS; INDOLES; MODELS, MOLECULAR; PROPANOLS; PYRROLES; RUTHENIUM COMPOUNDS; SULFONIC ACIDS;

EID: 51349142173     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja804379k     Document Type: Article

References (19)

1. (a) Gul, W.; Hamann, M. T. Life Sci. 2005, 78, 442-453.
2. (b) O'Connor, S. E.; Maresh, J. J. Nat. Prod. Rep. 2006, 23, 532-547.
3. (c) Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748-8758.
4. (d) Banwell, M. G.; Goodwin, T. E.; Ng, S.; Smith, J. A.; Wong, D. J. Eur. J. Org. Chem. 2006, 3043-3060.
5. (e) Fan, H.; Peng, J.; Hamann, M. T.; Hu, J.-F. Chem. Rev. 2008, 108, 264-287.
6. (a) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Org. Lett. 2004, 6, 3199-3202.
7. (b) Cheung, H. Y.; Yu, W.-Y.; Lam, F. L.; Au-Yeung, T. T. L.; Zhou, Z.; Chan, T. H.; Chan, A. S. C. Org. Lett. 2007, 9, 4295-4298.
8. Malkov, A. V.; Davis, S. L.; Baxendale, I. R.; Mitchell, W. L.; Kočovský, P. J. Org. Chem. 1999, 64, 2751-2764.
9. Liu, W.-B.; He, H.; Dai, L.-X.; You, S.-L. Org. Lett. 2008, 10, 1815-1818.
10. (a) Kimura, M.; Futamata, M.; Mukai, R.; Tamaru, Y. J. Am. Chem. Soc. 2005, 127, 4592-4593.
11. (b) Trost, B. M.; Quancard, J. J. Am. Chem. Soc. 2006, 128, 6314-6315.
12. (c) Kimura, M.; Fukasaka, M.; Tamaru, Y. Heterocycles 2006, 67, 535-542.
13. Usui, I.; Schmidt, S.; Keller, M.; Breit, B. Org. Lett. 2008, 10, 1207-1210.
14. Nieves, I. F.; Schott, D.; Gruber, S.; Pregosin, P. S. Helv. Chim. Acta 2007, 90, 271-276.
15. Zaitsev, A. B.; Gruber, S.; Pregosin, P. S. Chem. Commun. 2007, 4692-4693.
16. Fernandez, I.; Hermatschweiler, R.; Breher, F.; Pregosin, P. S.; Veiros, L. F.; Calhorda, M. J. Angew. Chem., Int. Ed. 2006, 45, 6386-6391.
17. (a) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
18. (b) The calculations were performed at the PBE1PBE/VDZP level using the Gaussian 03 package: Frisch, M. J. et al. Gaussian 03, revision C.02; Gaussian Inc.: Wallingford, CT, 2004.
19. 3CN and one sulfonate has two diastereomers (10 and 10′). These were shown to be equally stable (within 0.1 kcal/mol). Additional metric and electronic information for all calculated complexes (2, 10, 10′, and 11) are presented as Supporting Information (Table S1).