A new method for the synthesis of Z-enediones via IBX-mediated oxidative rearrangement of 2-alkynyl alcohol systems

Chemical Communications

Volumn , Issue 7, 2006, Pages 764-766

  Crone, Benedikt ^a   Kirsch, Stefan F ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKYNYL GROUP; BENZOIC ACID DERIVATIVE;

ARTICLE; MOLECULAR MECHANICS; OXIDATION KINETICS; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 32644485649     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b515838a     Document Type: Article

References (29)

1. For the synthesis of IBX, see: C. Hartmann and V. Meyer, Chem. Ber., 1893, 26, 1727;
2. M. Frigerio, M. Santagostino and S. Sputore, J. Org. Chem., 1999, 64, 4537.
3. For reviews, see: T. Wirth, Angew. Chem., Int. Ed., 2001, 40, 2812;
4. V. V. Zhdankin and P. J. Stang, Chem. Rev., 2002, 102, 2523;
5. I. Kumar, Synlett, 2005, 1488;
6. T. Wirth, Angew. Chem., Int. Ed., 2005, 44, 3656.
7. M. Frigerio and M. Santagostino, Tetrahedron Lett., 1994, 35, 8019;
8. S. De Munari, M. Frigerio and M. Santagostino, J. Org. Chem., 1996, 61, 9272;
9. J. D. More and N. S. Finney, Org. Lett., 2002, 4, 3001;
10. A. P. Thottumkara, M. S. Bowsher and T. K. Vinod, Org. Lett., 2005, 7, 2933.
11. K. C. Nicolaou, Y.-L. Zhong and P. S. Baran, Angew. Chem., Int. Ed., 2000, 39, 625;
12. K. C. Nicolaou, Y.-L. Zhong and P. S. Baran, Angew. Chem., Int. Ed., 2000, 39, 2525;
13. K. C. Nicolaou, Y.-L. Zhong and P. S. Baran, J. Am. Chem. Soc., 2001, 123, 3183;
14. K. C. Nicolaou, C. J. N. Mathison and T. Montagnon, J. Am. Chem. Soc., 2004, 126, 5192.
15. K. C. Nicolaou, T. Montagnon, P. S. Baran and Y.-L. Zhong, J. Am. Chem. Soc., 2002, 124, 2245;
16. K. C. Nicolaou, T. Montagnon and P. S. Baran, Angew. Chem., Int. Ed., 2002, 41, 993.
17. D. Magdziak, A. A. Rodriguez, R. W. Van De Water and T. R. R. Pettus, Org. Lett., 2002, 4, 285;
18. M. Shibuya, S. Ito, M. Takahashi and Y. Iwabuchi, Org. Lett., 2004, 6, 4303.
19. F. Mizukami, M. Ando, T. Tanka and J. Imamura, Bull. Chem. Soc. Jpn., 1978, 51, 335;
20. G. F. Koser, A. G. Relenyi, A. N. Kalos, L. Rebrovic and R. H. Wettach, J. Org. Chem., 1982, 47, 2487;
21. U. H. Hirt, M. F. H. Schuster, A. N. French, O. G. Wiest and T. Wirth, Eur. J. Org. Chem., 2001, 1569.
22. S. F. Kirsch, J. Org. Chem., 2005, 70, 10210.
23. M. Yamaguchi and I. Hirao, Tetrahedron Lett., 1983, 24, 391.
24. The formation of allene 5 was not observed in the IBX-mediated transformation 3b-n → 6b-n (Table 1, entries 2-14). In all cases, the corresponding 1,2-diketone 4 was detected as the major byproduct.
25. J. Levisalles, Bull. Soc. Chim. Fr., 1957, 79, 798;
26. B. M. Adger, C. Barrett, J. Brennan, M. A. McKervey and R. W. Murray, J. Chem. Soc., Chem. Commun., 1991, 1553;
27. M. K. Eberhardt, J. Org. Chem., 1993, 58, 497.
28. A. Del Zotto, W. Baratta, G. Verardo and P. Rigo, Eur. J. Org. Chem., 2000, 2795.
29. M. R. Sestrick, M. Miller and L. S. Hegedus, J. Am. Chem. Soc., 1992, 114, 4079.