Developments in nitrosocarbonyl chemistry: Mild oxidation of N-substituted hydroxylamines leads to new discoveries

Synthesis (Germany)

Volumn 46, Issue 3, 2014, Pages 269-280

  Palmer, Leoni I ^a   Frazier, Charles P ^a   De Alaniz, Javier Read ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

functionalization; aerobic oxidation; electrophilic synthon; hydroxylamines; nitroso

Indexed keywords

AEROBIC OXIDATIONS; FUNCTIONALIZATIONS; HYDROXYLAMINES; NITROSO; SYNTHONS;

AMINES; CATALYSIS; ESTERIFICATION; ESTERS;

OXIDATION;

1,2 OXAZINE DERIVATIVE; BETA KETO ESTER DERIVATIVE; COPPER DERIVATIVE; ELECTROPHILE; ESTER DERIVATIVE; HYDROXYLAMINE; NITROSO DERIVATIVE; NITROSOCARBONYL; NUCLEOPHILE; UNCLASSIFIED DRUG;

AMINATION; CATALYSIS; CATALYST; CHEMICAL REACTION; DIELS ALDER REACTION; FUNCTIONALIZATION REACTION; MICHAEL ADDITION; NITROSOCARBONYL ENE REACTION; OXIDATION; OXYGENATION; REVIEW; STEREOCHEMISTRY; SYNTHESIS; WITTIG REACTION;

EID: 84892930716     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0033-1338569     Document Type: Review

References (62)

1. Davis F. A., Chen B. C. Chem. Rev.: 1992; 92 919
2. Greck C., Genêt J. P. Synlett: 1997; 741
3. Dembech P., Seconi G., Ricci A. Chem. Eur. J.: 2000; 6 1281
4. Erdik E. Tetrahedron: 2004; 60 8747
5. Smith A. M. R, Hii K. K. Chem. Rev.: 2011; 111 1637
6. Gephart R. T., Warren T. H. Organometallics: 2012; 31 7728
7. Roizen J. L., Harvey M. E., Du Bois J. Acc. Chem. Res.: 2012; 45 911
8. Jeffrey J. L., Sarpong R. Chem. Sci.: 2013; 4 4092
9. Yamamoto H., Momiyama N. Chem. Commun.: 2005; 3514
10. Yamamoto H., Kawasaki M. Bull. Chem. Soc. Jpn.: 2007; 80 595
11. Iwasa S., Fakhruddin A., Nishiyama H. Mini-Rev. Org. Chem.: 2005; 2 157
12. Bodnar B. S., Miller M. J. Angew. Chem. Int. Ed.: 2011; 50 5630
13. Adam W., Krebs O. Chem. Rev.: 2003; 103 4131
14. Baidya M., Yamamoto H. Synthesis: 2013; 45 1931
15. Demond J. F., King S. B. Antioxid. Redox Signal.: 2011; 14 1637
16. Nakagawa H. Nitric Oxide: 2011; 25 195
17. Sutton A. D., Williamson M., Weismiller H., Toscano J. P. Org. Lett.: 2011; 14 472
18. Baidya M., Griffin K. A., Yamamoto H. J. Am. Chem. Soc.: 2012; 134 18566
19. Sandoval D., Frazier C. P., Bugarin A., Read de Alaniz J. J. Am. Chem. Soc.: 2012; 134 18948
20. Frazier C. P., Sandoval D., Palmer L. I., Read de Alaniz J. Chem. Sci.: 2013; 4 3857
21. Flower K. R., Lightfoot A. P., Wan H., Whiting A. Chem. Commun.: 2001; 1812
22. Iwasa S., Tajima K., Tsushima S., Nishiyama H. Tetrahedron Lett.: 2001; 42 5897
23. Adamo M. F. A, Bruschi S. J. Org. Chem.: 2007; 72 2666
24. Quadrelli P., Invernizzi A. G., Caramella P. Tetrahedron Lett.: 1996; 37 1909
25. Quadrelli P., Mella M., Caramella P. Tetrahedron Lett.: 1998; 39 3233
26. O'Bannon P. E., William D. P. Tetrahedron Lett.: 1988; 29 5719
27. O'Bannon P. E., Dailey W. P. J. Org. Chem.: 1989; 54 3096
28. Yashin N. V., Averina E. B., Grishin Y. K., Kuznetsova T. S., Zefirov N. S. Synthesis: 2006; 279
29. Chemagin A. V., Yashin N. V., Grishin Y. K., Kuznetsova T. S., Zefirov N. S. Synthesis: 2010; 259
30. So S. S., Mattson A. E. J. Am. Chem. Soc.: 2012; 134 8798
31. Keck G. E., Webb R. R., Yates J. B. Tetrahedron: 1981; 37 4007
32. Kirby G. W., McGuigan H., McLean D. J. Chem. Soc., Perkin Trans. 1: 1985; 1961
33. Kibayashi C., Aoyagi S. Synlett: 1995; 873
34. Yamamoto Y., Yamamoto H. Eur. J. Org. Chem.: 2006; 2031
35. Keck G. E., Webb R. R. J. Am. Chem. Soc.: 1981; 103 3173
36. Keck G. E., Webb R. R. J. Org. Chem.: 1982; 47 1302
37. Matsumura Y., Aoyagi S., Kibayashi C. Org. Lett.: 2003; 5 3249
38. Kalita B., Nicholas K. M. Tetrahedron Lett.: 2005; 46 1451
39. Atkinson D., Kabeshov M. A., Edgar M., Malkov A. V. Adv. Synth. Catal.: 2011; 353 3347
40. Kreβe G., Vasella A., Felber H., Ritter A., Ascherl B. Recl. Trav. Chim. Pays-Bas: 1986; 105 295
41. Braun H., Felber H., Kreβe G., Ritter A., Schmidtchen F. P., Schneider A. Tetrahedron: 1991; 47 3313
42. Yang B., Miller M. J. Tetrahedron Lett.: 2010; 51 328
43. Gouverneur V., Dive G., Ghosez L. Tetrahedron: Asymmetry: 1991; 2 1173
44. Chapuis C., Laumer J.-Y D. S, Marty M. Helv. Chim. Acta: 1997; 80 146
45. Vogt P. F., Miller M. J. Tetrahedron: 1998; 54 1317
46. Momiyama N., Yamamoto H. Angew. Chem. Int. Ed.: 2002; 41 2986
47. Brown S. P., Brochu M. P., Sinz C. J., MacMillan D. W. C. J. Am. Chem. Soc.: 2003; 125 10808
48. Hayashi Y., Yamaguchi J., Hibino K., Shoji M. Tetrahedron Lett.: 2003; 44 8293
49. Momiyama N., Yamamoto H. J. Am. Chem. Soc.: 2003; 125 6038
50. Zhong G. Angew. Chem. Int. Ed.: 2003; 42 4247
51. Momiyama N., Yamamoto H. J. Am. Chem. Soc.: 2004; 126 5360
52. Momiyama N., Yamamoto H. J. Am. Chem. Soc.: 2005; 127 1080
53. Kano T., Ueda M., Takai J., Maruoka K. J. Am. Chem. Soc.: 2006; 128 6046
54. Palomo C., Vera S., Velilla I., Mielgo A., Gómez-Bengoa E. Angew. Chem. Int. Ed.: 2007; 46 8054
55. Lu M., Zhu D., Lu Y., Zeng X., Tan B., Xu Z., Zhong G. J. Am. Chem. Soc.: 2009; 131 4562
56. Yanagisawa A., Takeshita S., Izumi Y., Yoshida K. J. Am. Chem. Soc.: 2010; 132 5328
57. Shen K., Liu X., Wang G., Lin L., Feng X. Angew. Chem. Int. Ed.: 2011; 50 4684
58. Kumarn S., Shaw D. M., Longbottom D. A., Ley S. V. Org. Lett.: 2005; 7 4189
59. Kumarn S., Shaw D. M., Ley S. V. Chem. Commun.: 2006; 3211
60. Unthank M. G., Hussain N., Aggarwal V. K. Angew. Chem. Int. Ed.: 2006; 45 7066
61. Kokotos C. G., McGarrigle E. M., Aggarwal V. K. Synlett: 2008; 2191
62. Yar M., McGarrigle E. M., Aggarwal V. K. Angew. Chem. Int. Ed.: 2008; 47 3784