Regio- and enantioselective allylation of indole catalyzed by a planar-chiral cyelopentadienyl-ruthenium complex

Chemistry Letters

Volumn 38, Issue 5, 2009, Pages 444-445

  Onitsuka, Kiyotaka ^a   Kameyama, Chiaki ^a   Sasai, Hiroaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 67650363887     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2009.444     Document Type: Article

References (29)

1. For reviews, see: B. M. Trost, D. L. V. Vranken, Chem. Rev. 1996, 96, 395;
2. G. Helmchen, J. Organomet. Chem. 1999, 576, 203;
3. B. M. Trost, J. Org. Chem. 2004, 69, 5813;
4. J. T. Mohr, B. M. Stoltz, Chem. Asian J. 2007, 2, 1476;
5. Z. Lu, S. Ma, Angew. Chem., Int. Ed. 2008, 47, 258.
6. For reviews, see: O. Belda, C. Moberg, Acc. Chem. Res. 2004, 37, 159;
7. C. Bruneau, J.-L. Renaud, B. Demerseman, Chem. - Eur. J. 2006, 12, 5178;
8. G. Helmchen, A. Dahnz, P. Dübon, M. Schelwies, R. Weihofen, Chem. Commun. 2007, 675.
9. N. Dodo, Y. Matsushima, M. Uno, K. Onitsuka, S. Takahashi, J. Chem. Soc, Dalton Trans. 2000, 35;
10. K. Onitsuka, N. Dodo, Y. Matsushima, S. Takahashi, Chem. Commun. 2001, 521;
11. K. Onitsuka, Y. Ajioka, Y. Matsushima, S. Takahashi, Organo- metallics 2001, 20, 3274;
12. Y. Matsushima, K. Onitsuka, S. Takahashi, Organometallics 2004, 23, 2439;
13. Y. Matsushima, K. Onitsuka, S. Takahashi, Organometallics 2004, 23, 3763.
14. Y. Matsushima, K. Onitsuka, T. Kondo, T. Mitsudo, S. Takahashi, J. Am. Chem. Soc. 2001, 123, 10405;
15. K. Onitsuka, Y. Matsushima, S. Takahashi, Organometallics 2005, 24, 6472.
16. K. Onitsuka, H. Okuda, H. Sasai, Angew. Chem., Int. Ed. 2008, 47, 1454.
17. A. V. Malkov, S. L. Davis, I. R. Baxendale, W. L. Mitchell, P. Kočovský, J. Org. Chem. 1999, 64, 2751;
18. M. Bandini, A. Melloni, A. Umani-Ronchi, Org. Lett. 2004, 6, 3199;
19. H. Y. Cheung, W.-Y. Yu, F. L. Lam, T. T.-L. Au-Yeung, Z. Zhou, T. H. Chan, A. S. C. Chan, Org. Lett. 2007, 9, 4295.
20. J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172;
21. J. Zhou, Y. Tang, J. Am. Chem. Soc. 2002, 124, 9030;
22. D. A. Evans, K. A. Scheidt, K. R. Fandrick, H. W. Lam, J. Wu, J. Am. Chem. Soc. 2003, 125, 10780;
23. R. P. Herrera, V. Sgarzani, L. Bernardi, A. Ricci, Angew. Chem., Int. Ed. 2005, 44, 6576;
24. B. M. Trost, J. Quancard, J. Am. Chem. Soc. 2006, 128, 6314;
25. B. M. Trost, Y. Zhang, J. Am. Chem. Soc. 2007, 129, 14548.
26. Recently, a similar reaction using chiral Ir catalysts was reported. W.-B. Liu, H. He, L.-X. Dai, S.-L. You, Org. Lett. 2008, 10, 1815.
27. Reactions of allyl alcohol derivatives with indole in the presence of achiral Ru catalysts were reported. S. Gruber, A. B. Zaitsev, M. Worle, P. S. Pregosin, L. F. Veiros, Organometallics 2008, 27, 3796;
28. A. B. Zaitsev, S. Gruber, P. A. Pluss, P. S. Pregosin, L. F. Veiros, M. Worle, J. Am. Chem. Soc. 2008, 130, 11604.
29. Supporting Information is also available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.