Electrophilic carbon transfer in gold catalysis: Synthesis of substituted chromones

Tetrahedron Letters

Volumn 52, Issue 19, 2011, Pages 2476-2479

  Renault, Jacques ^a   Qian, Zhao ^a   Uriac, Philippe ^a   Gouault, Nicolas ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

Chromones; Electrophilic transfer; Gold catalysis; Isomerisation

Indexed keywords

CARBON; CHROMONE DERIVATIVE; GOLD;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; ELECTROPHILIC CARBON TRANSFER; ELECTROPHILICITY; ISOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 79953703973     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.018     Document Type: Article

References (26)

1. N.D. Shapiro, and F.D. Toste Synlett 2010 675 691
2. A.S.K. Hashmi Angew. Chem., Int. Ed. 49 2010 5232 5241
3. A.S.K. Hashmi Chem. Rev. 107 2007 3180 3211
4. Z. Li, C. Brouwer, and C. He Chem. Rev. 108 2008 3239 3265
5. E. Jiménez-Nuňez, and A.M. Echavarren Chem. Rev. 108 2008 3326 3350
6. J. Muzart Tetrahedron 64 2008 5815 5849
7. D.J. Gorin, B.D. Sherry, and F.D. Toste Chem. Rev. 108 2008 3351 3378
8. A. Arcadi Chem. Rev. 108 2008 3266 3325
9. A. Fürstner, and P.W. Davies Angew. Chem., Int. Ed. 46 2007 3410 3449
10. I. Nakamura, T. Sato, and Y. Yamamoto Angew. Chem., Int. Ed. 45 2006 4473 4475
11. M. Vermura, I.D.G. Watson, M. Katsukawa, and F.D. Toste J. Am. Chem. Soc. 131 2009 3464 3465
12. I. Nakamura, T. Sato, M. Terada, and Y. Yamamoto Org. Lett. 9 2007 4081 4083
13. P. Garcia, M. Malacria, C. Aubert, V. Gandon, and L. Fensterbank ChemCatChem 2 2010 493 497
14. A.S. Bhat, J.L. Whetstone, and R.W. Brueggermeier Tetrahedron Lett. 40 1999 2469 2472
15. B. Bauvois, M. Puiffe, J.B. Bongui, S. Paillat, C. Monneret, and D. Dauzonne J. Med. Chem. 46 2003 3900 3913
16. H.P. Kim, K.H. Son, H.W. Chang, and S.S. Kang J. Pharmacol. Sci. 96 2004 229 245
17. C.J. Benett, S.T. Caldwell, D.B. McPhail, P.C. Morrice, G.G. Duthie, and R.C. Hartley Bioorg. Med. Chem. 12 2004 2079 2098
18. For the syntheses of compounds 1, 5a-i, see Supplementary materials.
19. M. Jean, J. Renault, P. van de Weghe, and N. Asao Tetrahedron Lett. 51 2010 378 381
20. K.H. Meyer, and K. Schuster Ber. Dtsch. Chem. Ges. 55B 1922 819 823
21. 3Na: 315.0997. Found 315.0994, (57%).
22. Spectral data of chromones or by-products are given in the Supplementary materials.
23. N. Asao, H. Aikawa, S. Tago, and K. Umetsu Org. Lett. 9 2007 4299 4302
24. I. Nakamura, T. Sato, M. Terada, and Y. Yamamoto Org. Lett. 10 2008 2649 2651
25. T. Jin, and Y. Yamamoto Org. Lett. 9 2007 5259 5262
26. J.-P. Bégué, and M. Malissard Tetrahedron 34 1978 2095 2103