Gold- or platinum-catalyzed tandem cycloisomerization/prins-type cyclization reactions

Angewandte Chemie - International Edition

Volumn 45, Issue 13, 2006, Pages 2091-2093

  Barluenga, José ^a   Diéguez, Alejandro ^a   Fernández, Amadeo ^a   Rodríguez, Félix ^a   Fañanás, Francisco J ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Carbocycles; Domino reactions; Gold; Homogeneous catalysis; Platinum

Indexed keywords

CATALYSIS; GOLD; PLATINUM; SUBSTITUTION REACTIONS;

CARBOCYCLES; DOMINO REACTIONS; HOMOGENEOUS CATALYSIS;

ISOMERIZATION;

EID: 33745661090     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503874     Document Type: Article

References (28)

1. a) L. F. Tietze, F. Hautner in Stimulating Concepts in Chemistry (Eds.: F. Vögtle, J. F. Stoddart, M. Shibasaki), Wiley-VCH, Weinheim, 2000, p. 38;
2. b) K. C. Nicolaou, E. W. Yue, T. Oshima in The New Chemistry (Ed.: N. Hall), Cambridge University Press, Cambridge, 2001, p. 168;
3. c) L. F. Tietze, Chem. Rev. 1996, 96, 115;
4. d) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 103;
5. Angew. Chem. Int. Ed. Engl. 1993, 32, 131.
6. For some recent reviews, see: a) C. Bruneau, Angew. Chem. 2005, 117, 2380;
7. Angew. Chem. Int. Ed. 2005, 44, 2328;
8. b) L. Añorbe, G. Domínguez, J. Pérez-Castells, Chem. Eur. J. 2004, 10, 4938;
9. c) S. T. Diver, A. J. Giessert, Chem. Rev. 2004, 104, 1317;
10. d) A. Echavarren, C. Nevado, Chem. Soc. Rev. 2004, 33, 431.
11. For a review, see: a) F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079;
12. b) B. Weyershausen, K. H. Dötz, Eur. J. Inorg. Chem. 1999, 1057;
13. c) F. E. McDonald, Chem. Eur. J. 1999, 5, 3103.
14. a) J. Barluenga, A. Diéguez, F. Rodríguez, F. J. Fañanás, T. Sordo, P. Campomanes, Chem. Eur. J. 2005, 11, 5735;
15. b) J. Barluenga, A. Diéguez, F. Rodríguez, F. J. Fañanás, Angew. Chem. 2005, 117, 128;
16. Angew. Chem. Int. Ed. 2005, 44, 126.
17. For some theoretical studies, see: T. Sordo, P. Campomanes, A. Diéguez, F. Rodríguez, F. J. Fañanás, J. Am. Chem. Soc. 2005, 127, 944, and ref. [4a].
18. Detailed studies on this issue will be published in due course. For a recent paper on the exo-cycloisomerization reaction of ω-alkynols catalyzed by iridium complexes, see: E. Genin, S. Antoniotti, V. Michelet, J.-P. Genêt, Angew. Chem. 2005, 117, 5029;
19. Angew. Chem. Int. Ed. 2005, 44, 4949.
20. For some recent interesting papers on the Prins reaction (and related reactions) see the following and references therein: a) R. Jasti, C. D. Anderson, S. C. Rychnovsky, J. Am. Chem. Soc. 2005, 127, 9939;
21. b) L. E. Overman, L. D. Pennington, J. Org. Chem. 2003, 68, 7143;
22. c) C. S. J. Barry, S. R. Crosby, J. R. Harding, R. A. Hughes, C. D. King, G. D. Parker, C. L. Willis, Org. Lett. 2003, 5, 2429.
23. The reactions with other metal complexes (Ru, Ir, Ni, In) were unsuccessful. However, promising preliminary results were obtained using silver and copper salts as catalysts.
24. It is worth pointing out that cyclizations analogous to those observed for 1-en-6-ynes without hydroxy groups have not been observed: M. P. Muñoz, M. Méndez, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Synthesis 2003, 2898.
25. For some references on alkynol activation by gold or platinum complexes, see: a) Y. Liu, F. Song, Z. Song, M. Liu, B. Yan, Org. Lett. 2005, 7, 5409;
26. b) J. H. Teles, S. Brode, M. Chabanas, Angew. Chem. 1998, 110, 1475;
27. Angew. Chem. Int. Ed. 1998, 37, 1415.
28. A simple hydrolysis of the carbon-metal bond could also be considered. See ref. [5] for computational studies on the cycloisomerization of ω-alkynols.