N-Heterocyclic carbene-catalyzed oxidations

Tetrahedron

Volumn 65, Issue 16, 2009, Pages 3102-3109

  Maki, Brooks E ^a   Chan, Audrey ^a   Phillips, Eric M ^a   Scheidt, Karl A ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYL ALCOHOL; BENZYL ALCOHOL; CARBENE; CARBOXYLIC ACID; ESTER; HETEROCYCLIC COMPOUND; MANGANESE; MANGANESE OXIDE; TRIAZOLE DERIVATIVE;

ACYLATION; ARTICLE; CATALYSIS; CHIRALITY; EPIMERIZATION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 62049085318     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.033     Document Type: Article

References (63)

1. Zhan B.Z., and Thompson A. Tetrahedron 60 (2004) 2917-2935
2. Caron P., Dugger R.W., Ruggeri S.G., Ragan J.A., and Ripin D.H.B. Chem. Rev. 106 (2006) 2943-2989
3. Sheldon R.A., Arends I., Ten Brink G.J., and Dijksman A. Acc. Chem. Res. 35 (2002) 774-781
4. Tojo G., and Fernández M. Oxidation of Alcohols to Aldehydes and Ketones (2006), Springer, New York, NY
5. Taylor R.J.K., Reid M., Foot J., and Raw S.A. Acc. Chem. Res. 38 (2005) 851-869
6. Gilman N.W. J. Chem. Soc., Chem. Commun. (1971) 733-734
7. Corey E.J., Katzenellenbogen J.A., Gilman N.W., Roman S.A., and Erickson B.W. J. Am. Chem. Soc. 90 (1968) 5618-5620
8. Corey E.J., Gilman N.W., and Ganem B.E. J. Am. Chem. Soc. 90 (1968) 5616-5617
9. Hünig S., and Schaller R. Angew. Chem., Int. Ed. Engl. 21 (1982) 36-49
10. Fisher M.J., Chow K., Villalobos A., and Danishefsky S.J. J. Org. Chem. 56 (1991) 2900-2907
11. Davidsen S.K., and Chumoyer M.Y. J. Org. Chem. 54 (1989) 5558-5567
12. Smith A.B., Sulikowski G.A., Sulikowski M.M., and Fujimoto K. J. Am. Chem. Soc. 114 (1992) 2567-2576
13. Corey E.J., and Samuelsson B. J. Org. Chem. 49 (1984) 4735
14. Mori N., and Togo H. Tetrahedron 61 (2005) 5915-5925
15. McDonald C., Holcomb H., Kennedy K., Kirkpatrick E., Leathers T., and Vanemon P. J. Org. Chem. 54 (1989) 1213-1215
16. Williams D.R., Klingler F.D., Allen E.E., and Lichtenthaler F.W. Tetrahedron Lett. 29 (1988) 5087-5090
17. Grigg R., Mitchell T.R.B., and Sutthivaiyakit S. Tetrahedron 37 (1981) 4313-4319
18. Marko I.E., Mekhalfia A., and Ollis W.D. Synlett (1990) 347-348
19. Ekoue-Kovi K., and Wolf C. Chem.-Eur. J. 14 (2008) 6302-6315
20. Sayama S., and Onami T. Synlett (2004) 2739-2745
21. Yoo W.J., and Li C.J. Tetrahedron Lett. 48 (2007) 1033-1035
22. Gopinath R., Barkakaty B., Talukdar B., and Patel B.K. J. Org. Chem. 68 (2003) 2944-2947
23. Travis B.R., Sivakumar M., Hollist G.O., and Borhan B. Org. Lett. 5 (2003) 1031-1034
24. Bal B.S., Childers W.E., and Pinnick H.W. Tetrahedron 37 (1981) 2091-2096
25. Reed L.J. Physiol. Rev. 33 (1953) 544-559
26. Sanadi D.R., Littlefield J.W., and Bock R.M. J. Biol. Chem. 197 (1952) 851-862
27. Hager L.P. J. Biol. Chem. 229 (1957) 251-263
28. Mizuhara S., Tamura R., and Arata H. Proc. Jpn. Acad. 87 (1951) 302-308
29. Castells J., Llitjos H., and Morenomanas M. Tetrahedron Lett. (1977) 205-206
30. Inoue H., and Higashiura K. J. Chem. Soc., Chem. Commun. (1980) 549-550
31. Yano Y., Tamura Y., Hoshino Y., and Tagaki W. Bull. Chem. Soc. Jpn. 53 (1980) 2340-2343
32. Tam S.W., Jimenez L., and Diederich F. J. Am. Chem. Soc. 114 (1992) 1503-1505
33. Miyashita A., Suzuki Y., Nagasaki I., Ishiguro C., Iwamoto K., and Higashino T. Chem. Pharm. Bull. 45 (1997) 1254-1258
34. Chan A., and Scheidt K.A. Org. Lett. 7 (2005) 905-908
35. Chan A., and Scheidt K.A. J. Am. Chem. Soc. 128 (2006) 4558-4559
36. Chan A., and Scheidt K.A. J. Am. Chem. Soc. 129 (2007) 5334-5335
37. Phillips E.M., Wadamoto M., Chan A., and Scheidt K.A. Angew. Chem., Int. Ed. 46 (2007) 3107-3110
38. Wadamoto M., Philllips E.M., Reynolds T.E., and Scheidt K.A. J. Am. Chem. Soc. 129 (2007) 10098-10099
39. Chan A., and Scheidt K.A. J. Am. Chem. Soc. 130 (2008) 2740-2741
40. Phillips E.M., Reynolds T.E., and Scheidt K.A. J. Am. Chem. Soc. 130 (2008) 2416-2417
41. Marion N., Diez-Gonzalez S., and Nolan S.P. Angew. Chem., Int. Ed. 46 (2007) 2988-3000
42. Enders D., Niemeier O., and Henseler A. Chem. Rev. 107 (2007) 5606-5655
43. Jones R.C.F., and Nichols J.R. Tetrahedron Lett. 31 (1990) 1771-1774
44. Attenburrow J., Cameron A.F.B., Chapman J.H., Evans R.M., Hems B.A., Jansen A.B.A., and Walker T.J. J. Chem. Soc. (1952) 1094-1111
45. Fatiadi A.J. Synthesis (1976) 133-167
46. Fatiadi A.J. Synthesis (1976) 65-104
47. Maki B.E., Chan A., Phillips E.M., and Scheidt K.A. Org. Lett. 9 (2007) 371-374
48. Maki B.E., and Scheidt K.A. Org. Lett. 10 (2008) 4331-4334
49. Song J.J., Tan Z.L., Reeves J.T., Yee N.K., and Senanayake C.H. Org. Lett. 9 (2007) 1013-1016
50. Reynolds T.E., Stern C.A., and Scheidt K.A. Org. Lett. 9 (2007) 2581-2584
51. Zhao M.Z., Li J., Mano E., Song Z.G., Tschaen D.M., Grabowski E.J.J., and Reider P.J. J. Org. Chem. 64 (1999) 2564-2566
52. Wilson S.R., Tofigh S., and Misra R.N. J. Org. Chem. 47 (1982) 1360-1361
53. Frost C.G., and Hartley B.C. Org. Lett. 9 (2007) 4259-4261
54. Ley S.V., Norman J., Griffith W.P., and Marsden S.P. Synthesis (1994) 639-666
55. Noonan C., Baragwanath L., and Connon S.J. Tetrahedron Lett. 49 (2008) 4003-4006
56. Foot J.S., Kanno H., Giblin G.M.P., and Taylor R.J.K. Synthesis (2003) 1055-1064
57. Foot J.S., Kanno H., Giblin G.M.P., and Taylor R.J.K. Synlett (2002) 1293-1295
58. Wuts P.G.M., and Greene T.W. Protective Groups in Organic Synthesis. 4th ed. (2007), Wiley & Sons, Hoboken, NJ
59. Pearson A.J., and Lee K.S. J. Org. Chem. 59 (1994) 2304-2313
60. Woodward R.B., Heusler K., Gosteli J., Naegeli P., Oppolzer W., Ramage R., Ranganat S., and Vorbrugg H. J. Am. Chem. Soc. 88 (1966) 852-853
61. Sieber P. Helv. Chim. Acta 60 (1977) 2711-2716
62. Gewehr M., and Kunz H. Synthesis (1997) 1499-1511
63. Reynolds N.T., de Alaniz J.R., and Rovis T. J. Am. Chem. Soc. 126 (2004) 9518-9519