A broadly applicable mild method for the synthesis of gem-diperoxides from corresponding Ketones or 1,3-dioxolanes

Organic Letters

Volumn 11, Issue 7, 2009, Pages 1615-1618

  Li, Yun ^a   Hao, H D ^a   Zhang, Qi ^a   Wu, Yikang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; KETONE; MOLYBDENUM; PEROXIDE; PHOSPHOMOLYBDIC ACID; PHOSPHORIC ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; DIOXOLANES; KETONES; MOLECULAR STRUCTURE; MOLYBDENUM; PEROXIDES; PHOSPHORIC ACIDS;

EID: 64349109464     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900262t     Document Type: Article

References (36)

1. (a) Liu, J.-M.; Ni, M.-Y.; Fan, J.-F.; Tu, Y.-Y.; Wu, Z.-H.; Wu, Y.-L.; Chou, W.-S. Acta Chim. Sin. 1979, 37, 129-143.
2. (Chem. Abstr. 1980, 92, 94594w).
3. (b) Klayman, D. L. Science 1985, 228, 1049-1055.
4. (c) Haynes, R. K.; Vonwiller, S. C. Acc. Chem. Res. 1997, 30, 73-79.
5. (d) Vroman, J. A.; Alvim-Gaston, M.; Avery, M. A. Curr. Pharm. Des. 1999, 5, 101-138.
6. (e) Robert, A.; Dechy-Cabaret, O.; Cazalles, J. M.; Meunier, B. Acc. Chem. Res. 2002, 35, 167-174.
7. (f) Li, Y.; Wu, Y.-L. Curr. Med. Chem. 2003, 10, 2197-2230.
8. (g) O'Neill, P. M.; Posner, G. H. J. Med. Chem. 2004, 47, 2945-2964.
9. (h) Posner, G. H.; O'Neill, P. M. Acc. Chem. Res. 2004, 37, 397-404.
10. (i) Tang, Y.; Dong, Y.; Vennerstrom, J. L. Med. Res. Rev. 2004, 24, 425-448.
11. (j) Muraleedharan, K. M.; Avery, M. A. ComprehensiVe Med. Chem. II 2006, 7, 765-814.
12. (a) Kim, H.-S.; Tsuchiya, K.; Shibata, Y.; Wataya, Y.; Ushigoe, Y.; Masuyama, A.; Nojima, M.; McCullough, K. J. J. Chem. Soc., Perkin Trans. 1 1999, 1867-1870.
13. (b) Hamada, Y.; Tokuhara, H.; Masuyama, A.; Nojima, M.; Kim, H.-S.; Ono, K.; Ogura, N.; Wataya, Y. J. Med. Chem. 2002, 45, 1374-1378.
14. (c) Kim, H.-S.; Nagai, Y.; Ono, K.; Begum, K.; Wataya, Y.; Hamada, Y.; Tsuchiya, K.; Masuyama, A.; Nojima, M; McCullough, K. J. J. Med. Chem. 2001, 44, 2357-2361.
15. (d) Vennerstrom, J. L.; Dong, Y.; Andersen, S. L.; Ager, A. L., Jr.; Fu, H.-n.; Miller, R. E.; Wesche, D. L.; Kyle, D. E.; Gerena, L.; Walters, S. M.; Wood, J. K.; Edwards, G.; Holme, A. D.; McLean, W. G.; Milhous, W. K. J. Med. Chem. 2000, 43, 2753-2758.
16. (e) Tsuchiya, K.; Hamada, Y.; Masuyama, A.; Nojima, M. Tetrahedron Lett. 1999, 40, 4077-4080.
17. (f) Dong, Y.; Matile, H.; Chollet, J.; Kaminsky, R.; Wood, J. K.; Vennerstrom, J. L. J. Med. Chem. 1999, 42, 1477-1480.
18. (g) Kim, H. S.; Tsuchiya, K.; Shibata, Y.; Wataya, Y.; Ushigoe, Y.; Masuyama, A.; Nojima, M.; McCullough, K. J. J. Chem. Soc. Perkin Trans. 1 1999, 1867-1870.
19. (a) Ledaal, T.; Solbjor, T. Acta Chem. Scand. 1967, 21, 1658-1659.
20. (b) Ramirez, A.; Woerpel, K. A. Org. Lett. 2005, 7, 4617-4620.
21. (c) Terent'ev, A. O.; Platonov, M. M.; Ogibin, Y. N.; Nikishin, G. I. Synth. Commun. 2007, 37, 1281-1287.
22. (d) Jefford, C. W.; Li, Y.; Jaber, A.; Boukouvalas, J. Synth. Commun. 1990, 20, 2589-2596.
23. (e) Das, B.; Veeranjaneyulu, B.; Krishnaiah, M.; Balasubramanyam, P. J. Mol. Catal. A 2008, 284, 116-119.
24. (f) Terent'ev, A. O.; Kutkin, A. V.; Platonov, M. M.; Ogibin, Y. N.; Nikishin, G. I. Tetrahedron Lett. 2003, 44, 7359-7363.
25. (g) Bunge, A.; Hamann, H.-J.; Liebscher, J. Tetrahedron Lett. 2009, 50, 524-526.
26. (h) Das, B.; Krishnaiah, M.; Veeranjaneyulu, B.; Ravikanth, B. Tetrahedron Lett. 2007, 48, 6286-6289.
27. (i) Zmitek, K.; Zupan, M.; Stavber, S.; Iskra, J. Org. Lett. 2006, 8, 2491-2494.
28. (j) Iskra, J.; Bonnet-Delponb, D.; Bégué, J.-P. Tetrrahedron Lett. 2003, 44, 6309-6312.
29. (k) Ghorai, P.; Dussault, P. H. Org. Lett. 2008, 10, 4577-4579.
30. (l) Zmitek, K.; Zupana, M.; Iskra, J. Org. Biomol. Chem 2007, 5, 3895-3908. (a review).
31. (m) Ghorai, P.; Dussault, P. H. Org. Lett. 2009, 11, 213-216.
32. (a) Saito, I.; Nagata, R.; Yuba, K.; Matsuura, T. Tetrahedron Lett. 1983, 24, 1737-1740.
33. (b) Terent'ev, A. O.; Krylov, I. B.; Borisov, D. A.; Nikishin, G. I. Synthesis 2007, 2979-2986.
34. (c) Liu, Y.-H.; Zhang, Z.-H.; Li, T.-S. Synthesis 2008, 3314-3318.
35. (d) Ref 3d. For modification made in this work, see the Supporting Information.
36. The only exception was found in ref 3d (a compound similar to 5r but without the aromatic ring and the oxygen in the six-membered ring).