PtCl2-Catalyzed Cycloisomerizations of Allenynes

Journal of the American Chemical Society

Volumn 126, Issue 11, 2004, Pages 3408-3409

  Cadran, Nicolas ^a   Cariou, Kevin ^a   Hervé, Gwénaëlle ^a   Aubert, Corinne ^a   Fensterbank, Louis ^a   Malacria, Max ^a   Marco Contelles, José ^b  

^a SORBONNE UNIVERSITÉ   (France)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ALLENE DERIVATIVE; ALLENYNE DERIVATIVE; DEUTERIUM; PLATINUM DERIVATIVE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CYCLIZATION; ISOMERIZATION; ISOTOPE LABELING; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 1642264283     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja031892g     Document Type: Article

References (31)

1. For recent contributions, see: (a) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104.
2. (b) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801.
3. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511.
4. (d) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757.
5. (e) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863.
6. (f) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
7. Mainetti, E.; Mouriès, V.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. Angew. Chem., Int. Ed. 2002, 41, 2132.
8. (a) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397.
9. (b) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215.
10. (c) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627.
11. (a) Cao, H.; Flippen-Anderson, J.; Cook, J. M. J. Am. Chem. Soc. 2003, 125, 3230.
12. (b) Brummond, K. M.; Kerekes, A. D.; Wan, H. J. Org. Chem. 2002, 67, 5156.
13. (c) Pagenkopf, B. L.; Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse, T. Synthesis 2000, 1009.
14. (d) Mukai, C.; Nomura, I.; Kitagaki, S. J. Org. Chem. 2003, 68, 1376.
15. (e) Shibata, T.; Kadowaki, S.; Hirase, M.; Takagi, K. Synlett 2003, 573.
16. Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
17. Llerena, D.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1996, 37, 7027.
18. Brummond, K. M.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186.
19. (a) Oh, C. H.; Jung, S. H.; Rhim, C. Y. Tetrahedron Lett. 2001, 42, 8669.
20. (b) Shin, S.; RajanBabu, T. V. J. Am. Chem. Soc. 2001, 123, 8416.
21. Shibata, T.; Takesue, Y.; Kadowaki, S.; Takagi, K. Synlett 2003, 268.
22. (a) Urabe, H.; Takeda, T.; Hideura, D.; Sato, F. J. Am. Chem. Soc. 1997, 119, 11295.
23. (b) Yamazaki, T.; Urabe, H.; Sato, F. Tetrahedron Lett. 1998, 39, 7333.
24. For a 5-endo-trig cyclization involving a vinylcopper species, see: Huang, X.; Zhou, H. Org. Lett. 2002, 4, 4419.
25. For a study on β-elimination involving palladium complexes, see: Trost, B. M.; Tanoury, G. H.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255.
26. Presumably platinum(IV) complex a is octahedral. The metal center here is coordinatively unsaturated, with two mutually trans chlorides, while the allylic C-H would coordinate (agostic bond) with one of the vacant coordination sites of Pt(IV) (trans to the alkyl). We thank one of the referees for this preliminary rationalization of the regioselective hydrogen elimination.
27. Bertrand, M.; Dulcère, J.-P.; Grimaldi, J.; Malacria, M. C. R. Acad. Sci. Fr., Ser. C 1974, 279, 805.
28. Muccio, D. D.; Brouillette, W. J.; Alam, M.; Vaezi, M. F.; Sani, B. P.; Venepally, P.; Reddy, L.; Li, E.; Norris, A. W.; Simpson-Herren, L.; Hill, D. L. J. Med. Chem. 1996, 39, 3625.
29. For further elements on this reaction, see: Cariou, K.; Fensterbank, L.; Lopez-Romero, J. M.; Mainetti, E.; Mouriès, V.; Malacria, M.; Anjum, S.; Marco-Contelles, J., to be published. See also: Miki, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2003, 68, 8505 and ref 10 therein.
30. For further elements on this reaction, see: Cariou, K.; Fensterbank, L.; Lopez-Romero, J. M.; Mainetti, E.; Mouriès, V.; Malacria, M.; Anjum, S.; Marco-Contelles, J., to be published. See also: Miki, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2003, 68, 8505 and ref 10 therein.
31. Adduct 14 is contaminated by 5-10% of the hydrolyzed Alder-ene adduct.