Synthesis of silyl monoperoxyketals by regioselective cobalt-catalyzed peroxidation of silyl enol ethers: Application to the synthesis of 1,2-dioxolanes

Organic Letters

Volumn 16, Issue 16, 2014, Pages 4280-4283

  Hurlocker, Brisa ^a   Miner, Matthew R ^a   Woerpel, K A ^a  

^a NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; COBALT; ETHER DERIVATIVE; SILANE DERIVATIVE;

CATALYSIS; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; SYNTHESIS;

CATALYSIS; COBALT; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; DIOXOLANES; ETHERS; SILANES;

EID: 84906232252     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5020015     Document Type: Article

References (38)

1. Casteel, D. A. Nat. Prod. Rep. 1999, 16, 55
2. Liu, D.-Z.; Liu, J.-K. Nat. Prod. Bioprospect. 2013, 3, 161
3. Martyn, D. C.; Beletsky, G.; Cortese, J. F.; Tyndall, E.; Liu, H.; Fitzgerald, M. M.; O'Shea, T. J.; Liang, B.; Clardy, J. Bioorg. Med. Chem. Lett. 2009, 19, 5657
4. Vennerstrom, J. L.; Arbe-Barnes, S.; Brun, R.; Charman, S. A.; Chiu, F. C. K.; Chollet, J.; Dong, Y.; Dorn, A.; Hunziker, D.; Matile, H.; McIntosh, K.; Padmanilayam, M.; Santo Tomas, J.; Scheurer, C.; Scorneaux, B.; Tang, Y.; Urwyler, H.; Wittlin, S.; Charman, W. N. Nature 2004, 430, 900
5. Chen, Y.; McCarthy, P. J.; Harmody, D. K.; Schimoler-O'Rourke, R.; Chilson, K.; Selitrennikoff, C.; Pomponi, S. A.; Wright, A. E. J. Nat. Prod. 2002, 65, 1509
6. Horton, P. A.; Longley, R. E.; Kelly-Borges, M.; McConnell, O. J. J. Nat. Prod. 1994, 57, 1374
7. Bach, R. D.; Ayala, P. Y.; Schlegel, H. B. J. Am. Chem. Soc. 1996, 118, 12758
8. Terent'ev, A. O.; Borisov, D. A.; Vil', V. A.; Dembitsky, V. M. Beilstein J. Org. Chem. 2014, 10, 34
9. McCullough, K. J.; Nojima, M. Curr. Org. Chem. 2001, 5, 601
10. Tian, X.-Y.; Han, J.-W.; Zhao, Q.; Wong, H. N. C. Org. Biomol. Chem. 2014, 12, 3686
11. Sun, X.-Y.; Tian, X.-Y.; Li, Z.-W.; Peng, X.-S.; Wong, H. N. C. Chem. - Eur. J. 2011, 17, 5874
12. Dussault, P. H.; Liu, X. Org. Lett. 1999, 1, 1391
13. Dussault, P. H.; Lee, H.-J.; Niu, Q. J. J. Org. Chem. 1995, 60, 784
14. Martyn, D. C.; Ramirez, A. P.; Beattie, M. J.; Cortese, J. F.; Patel, V.; Rush, M. A.; Woerpel, K. A.; Clardy, J. Bioorg. Med. Chem. Lett. 2008, 18, 6521
15. Dussault, P. H.; Lee, I. Q. J. Am. Chem. Soc. 1993, 115, 6458
16. Kandur, W. V.; Richert, K. J.; Rieder, C. J.; Thomas, A. M.; Hu, C.; Ziller, J. W.; Woerpel, K. A. Org. Lett. 2014, 16, 2650
17. Li, Y.; Wittlin, S.; Wu, Y. Heterocycles 2012, 86, 245
18. Wang, X.; Dong, Y.; Wittlin, S.; Creek, D.; Chollet, J.; Charman, S. A.; Santo Tomas, J.; Scheurer, C.; Snyder, C.; Vennerstrom, J. L. J. Med. Chem. 2007, 50, 5840
19. Ramirez, A.; Woerpel, K. A. Org. Lett. 2005, 7, 4617
20. Dussault, P. H.; Lee, I. Q.; Lee, H.-J.; Lee, R. J.; Niu, Q. J.; Schultz, J. A.; Zope, U. R. J. Org. Chem. 2000, 65, 8407
21. ŹŒmitek, K.; Zupan, M.; Iskra, J. Org. Biomol. Chem. 2007, 5, 3895
22. Dussault, P. H.; Davies, D. R. Tetrahedron Lett. 1996, 37, 463
23. ŹŒmitek, K.; Zupan, M.; Stavber, S.; Iskra, J. J. Org. Chem. 2007, 72, 6534
24. Isayama, S. Bull. Chem. Soc. Jpn. 1990, 63, 1305
25. Silva, E. M. P.; Pye, R. J.; Cardin, C.; Harwood, L. M. Synlett 2010, 509
26. Barnych, B.; Fenet, B.; Vatele, J.-M. Tetrahedron 2013, 69, 334
27. Barnych, B.; Vatele, J.-M. Org. Lett. 2012, 14, 564
28. O'Neill, P. M.; Pugh, M.; Davies, J.; Ward, S. A.; Park, B. K. Tetrahedron Lett. 2001, 42, 4569
29. Tokuyasu, T.; Kunikawa, S.; McCullough, K. J.; Masuyama, A.; Nojima, M. J. Org. Chem. 2005, 70, 251
30. Tokuyasu, T.; Kunikawa, S.; Masuyama, A.; Nojima, M. Org. Lett. 2002, 4, 3595
31. Hioe, J.; Zipse, H. In Encyclopedia of Radicals in Chemistry, Biology and Materials; Chatgilialoglu, C.; Studer, A., Eds.; Wiley: Hoboken, NJ, 2012; Vol. 1, pp 449-476.
32. Nelson, T. D.; Crouch, R. D. Synthesis 1996, 1031
33. Battino, R.; Rettich, T. R.; Tominaga, T. J. Phys. Chem. Ref. Data 1983, 12, 163
34. O'Neill, P. M.; Hindley, S.; Pugh, M. D.; Davies, J.; Bray, P. G.; Park, B. K.; Kapu, D. S.; Ward, S. A.; Stocks, P. A. Tetrahedron Lett. 2003, 44, 8135
35. Maeda, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1997, 62, 6429
36. Shambayati, S.; Blake, J. F.; Wierschke, S. G.; Jorgensen, W. L.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 697
37. Smitrovich, J. H.; Woerpel, K. A. Synthesis 2002, 2778
38. Dussault, P. H.; Zope, U. Tetrahedron Lett. 1995, 36, 3655