Stereoselective isoxazolidine synthesis via copper-catalyzed alkene aminooxygenation

Journal of Organic Chemistry

Volumn 77, Issue 17, 2012, Pages 7755-7760

  Karyakarte, Shuklendu D ^a   Smith, Thomas P ^a   Chemler, Sherry R ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BIOLOGY; DIASTEREOSELECTIVITIES; DRUG DISCOVERY; ISOXAZOLIDINES; ORGANIC SYNTHESIS; STEREO-SELECTIVE; STEREOSELECTIVE SYNTHESIS;

CATALYSIS; COPPER; OLEFINS; STEREOCHEMISTRY;

STEREOSELECTIVITY;

ALKENE DERIVATIVE; COPPER; GAMMA LACTONE DERIVATIVE; HYDROXYLAMINE; ISOXAZOLIDINE DERIVATIVE; N SULFONYL O BUTENYL HYDROXYLAMINE; N,N,N TRIMETHYLTEMPAMINE; NITROGEN; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; DRUG DEVELOPMENT; ENANTIOSELECTIVITY; OXIDATION REDUCTION REACTION; OXYGENATION; STEREOCHEMISTRY; SYNTHESIS;

ALKENES; AMINES; CATALYSIS; COPPER; CYCLIZATION; MOLECULAR STRUCTURE; OXAZOLES; OXYGEN; STEREOISOMERISM;

EID: 84866098271     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3013226     Document Type: Article

References (43)

1. Nora, G. P.; Miller, M. J.; Mollmann, U. Bioorg. Med. Chem. Lett. 2006, 16, 3966-3970
2. Lee, L. W.; Taylor, C. E. C.; Desaulniers, J.-P.; Zhang, M.; Hojfeldt, J. W.; Pan, Q.; Mapp, A. K. Bioorg. Med. Chem. Lett. 2009, 19, 6233-6236
3. Loh, B.; Vozzolo, L.; Mok, B. J.; Lee, C. C.; Fitzmaurice, R. J.; Caddick, S.; Fassati, A. Chem. Biol. Drug Des. 2010, 75, 461-474
4. Rescifina, A.; Chiacchio, U.; Corsaro, A.; Piperno, A.; Romeo, R. Eur. J. Med. Chem. 2011, 46, 129-136
5. Martin, J. N.; Jones, R. C. F. Synthetic Application of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A.; Pearson, W. H., Eds.; Wiley and Sons: Hoboken, NJ, 2003; Chapter 1, p 1.
6. Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863-909
7. Stanley, L. M.; Sibi, M. P. Chem. Rev. 2008, 108, 2887-2902
8. Evans, D. A.; Song, H.-J.; Fandrick, K. R. Org. Lett. 2006, 8, 3351-3354
9. Kano, T.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2005, 127, 11926-11927
10. Kanemasa, S.; Oderaotoshi, Y.; Tanaka, J.; Wada, E. J. Am. Chem. Soc. 1998, 120, 12355-12356
11. Kobayashi, S.; Kawamura, M. J. Am. Chem. Soc. 1998, 120, 5840-5841
12. Suga, H.; Nakajima, T.; Itho, K.; Kakehi, A. Org. Lett. 2005, 7, 1431-1434
13. Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874-9875
14. Karlsson, S.; Hogberg, H.-E. Eur. J. Org. Chem. 2003, 2782-2791
15. Desimoni, G.; Faita, G.; Toscanini, M.; Boiocchi, M. Chem. - Eur. J. 2009, 15, 9674-9677
16. Barroso, S.; Blay, G.; Munoz, M. C.; Pedro, J. R. Org. Lett. 2011, 13, 402-405
17. Chatterjee, I.; Frohlich, R.; Studer, A. Angew. Chem., Int. Ed. 2011, 50, 11257-11260
18. Bates, R. W.; Sa-Ei, K. Org. Lett. 2002, 4, 4225-4227
19. Dongol, K. G.; Tay, B. Y.; Xiang, K. Synth. Commun. 2006, 36, 1247-1257
20. Dongo, K. G.; Tay, B. Y. Tetrahedron Lett. 2006, 47, 927-930
21. Hay, M. B.; Wolfe, J. P. Angew. Chem., Int. Ed. 2007, 46, 6492-6494
22. Lemen, G. S.; Giampietro, N. C.; Hay, M. B.; Wolfe, J. P. J. Org. Chem. 2009, 74, 2533-2540
23. Bates, R.; Nemeth, J.; Snell, R. Synthesis 2008, 1033-1038
24. Bates, R. W.; Lu, Y. Org. Lett. 2010, 12, 3938-3941
25. LeLonde, R. L.; Wang, Z. J.; Mba, M.; Lackner, A. D.; Toste, F. D. Angew. Chem., Int. Ed. 2010, 49, 598-601
26. Peng, J.; Lin, W.; Yuan, S.; Chen, Y. J. Org. Chem. 2007, 72, 3145-3148
27. Malkov, A. V.; Barlog, M.; Miller-Potucka, L.; Kabeshov, M. A.; Farrugia, L. J.; Kocovsky, P. Chem. - Eur. J. 2012, 18, 6873-6884
28. Moriyama, K.; Izumisawa, Y.; Togo, H. J. Org. Chem. 2011, 76, 7249-7255
29. Janza, B.; Studer, A. Synthesis 2002, 2117-2123
30. Fuller, P. H.; Kim, J.-W.; Chemler, S. R. J. Am. Chem. Soc. 2008, 130, 17638-17639
31. Paderes, M. C.; Chemler, S. R. Org. Lett. 2009, 11, 1915-1918
32. Paderes, M. C.; Chemler, S. R. Eur. J. Org. Chem. 2011, 3679-3684
33. Paderes, M. C.; Belding, L.; Fanovic, B.; Dudding, T.; Keister, J. B.; Chemler, S. R. Chem. - Eur. J. 2012, 18, 1711-1726
34. Sequeira, F. C.; Bovino, M. T.; Chipre, A. J.; Chemler, S. R. Synthesis 2012, 44, 1481-1484
35. Tufariello, J. J.; Lee, G. E. J. Am. Chem. Soc. 1980, 102, 373-374
36. Cicchi, S.; Bonanni, M.; Cardona, F.; Revuelta, J.; Goti, A. Org. Lett. 2003, 5, 1773-1776 and references therein.
37. Degiorgis, F.; Lombardo, M.; Trombini, C. Synthesis 1997, 1243-1245
38. Duris, A.; Wiesenganger, T.; Moravcikova, D.; Baran, P.; Kozisek, J.; Daich, A.; Berkes, D. Org. Lett. 2011, 13, 1642-1645
39. Yus, M.; Gonzalez-Gomez, J. C.; Foubelo, F. Chem. Rev. 2011, 111, 7774-7854
40. Taillier, C.; Hameury, T.; Bellosta, V.; Cossy, J. Tetrahedron 2007, 63, 4472-4490
41. Liu, K.; Aricho, J. W.; Taylor, R. E. J. Org. Chem. 2010, 75, 3953-3957
42. Lin, M.; Lin, L.; Chuang, T. Synlett 2011, 1871-1874
43. Dussault, P.; Shchepin, R.; Xu, C. Org. Lett. 2010, 12, 4772-4775