Oxidative Rearrangements with Hypervalent Iodine Reagents

Synthesis (Germany)

Volumn 45, Issue 18, 2013, Pages 2499-2511

  Singh, Fateh V ^a   Wirth, Thomas ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

hypervalent iodine reagents; oxidative rearrangements; ring contractions; ring expansions

Indexed keywords

HOFMANN REARRANGEMENT; HYPERVALENT IODINE CHEMISTRY; HYPERVALENT IODINE REAGENTS; OXIDATIVE CYCLIZATION; OXIDATIVE REARRANGEMENTS; RING CONTRACTION; RING EXPANSION; WAGNER-MEERWEIN REARRANGEMENT;

CYCLIZATION; REACTION KINETICS; SCAFFOLDS;

IODINE;

ALCOHOL DERIVATIVE; IODINE; NUCLEOPHILE; REAGENT; ROFECOXIB; SPIRONOLACTONE; UREA DERIVATIVE;

CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DIMERIZATION; DOMINO REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ELIMINATION REACTION; ENANTIOSELECTIVITY; HOFMANN REARRANGEMENT; OXIDATION; OXIDATIVE REARRANGEMENT; REVIEW; RING CONTRACTION; RING EXPANSION; STEREOCHEMISTRY; WAGNER MEERWEIN REARRANGEMENT;

EID: 84883770251     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0033-1339679     Document Type: Review

References (49)

1. Wirth T. Angew. Chem. Int. Ed.: 2001; 40 2812; Angew. Chem. 2001, 113, 2893
2. Zhdankin V. V. Chem. Rev.: 2002; 102 2523
3. Wirth T. In Organic Synthesis Highlights V. Schmalz H.-G, Wirth T. Wiley-VCH Weinheim: 2003; 144
4. Topics in Current Chemistry. Vol. 224 Wirth T. Springer Berlin: 2003
5. Wirth T. Angew. Chem. Int. Ed.: 2005; 44 3656; Angew. Chem. 2005, 117, 3722
6. Moriarty R. M. J. Org. Chem.: 2005; 70 2893
7. Ladziata U., Zhdankin V. V. Synlett: 2007; 527
8. Yusubov M. S., Zhdankin V. V. Curr. Org. Synth.: 2012; 9 247
9. Merritt E. A., Olofsson B. Angew. Chem. Int. Ed.: 2009; 48 9052; Angew. Chem. 2009, 121, 9214
10. Uyanik M., Ishihara K. Chem. Commun.: 2009; 45 2086
11. Satam V., Harad A., Rajule R., Pati H. Tetrahedron: 2010; 66 7659
12. Liang H., Ciufolini M. A. Tetrahedron: 2010; 66 5884
13. Merritt E. A., Olofsson B. Synthesis: 2011; 517
14. Brown M., Farid U., Wirth T. Synlett: 2013; 24 424
15. Singh F. V., Wirth T. In Comprehensive Organic Chemistry II. Knochel P. Elsevier Amsterdam: 2013; in press; and references cited therein
16. Zhdankin V. V. Chem. Rev.: 2008; 108 5299
17. Zhdankin V. V. ARKIVOC: 2009; (i) 1
18. Zhang L.-H, Kauffman G. S., Pesti J. A., Yin J. J. Org. Chem.: 1997; 62 6918
19. Berkessel A., Glaubitz K., Lex J. Eur. J. Org. Chem.: 2002; 2948
20. Loudon G. M., Radhakrishna A. S., Almond M. R., Blodgett J. K., Boutin R. H. J. Org. Chem.: 1984; 49 4272
21. Boutin R. H., Loudon G. M. J. Org. Chem.: 1984; 49 4277
22. Lazbin I. M., Koser G. F. J. Org. Chem.: 1986; 51 2669
23. Lazbin I. M., Koser G. F. J. Org. Chem.: 1987; 52 476
24. Vasudevan A., Koser G. F. J. Org. Chem.: 1988; 53 5158
25. Moriarty R. M., Chany C. J. II, Vaid R. K., Prakash O., Tuladhar S. M. J. Org. Chem.: 1993; 58 2478
26. Della E. W., Head N. J. J. Org. Chem.: 1995; 60 5303
27. Ramsden C. A., Rose H. L. J. Chem. Soc., Perkin Trans. 1: 1997; 2319
28. Davis M. C., Stasko D., Chapman R. D. Synth. Commun.: 2003; 33 2677
29. Tohma H., Maruyama A., Maeda A., Maegawa T., Dohi T., Shiro M., Morita T., Kita Y. Angew. Chem. Int. Ed.: 2004; 43 3595; Angew. Chem. 2004, 116, 3679
30. Andruszkiewicz R., Rozkiewicz D. Synth. Commun.: 2004; 34 1049
31. Yamada K., Urakawa H., Oku H., Katakai R. J. Pept. Res.: 2004; 64 43
32. Liu S. J., Zhang J. Z., Tian G. R., Liu P. Synth. Commun.: 2005; 36 823
33. Yusubov M. S., Funk T. V., Chi K.-W, Cha E.-H, Kim G. H., Kirschning A., Zhdankin V. V. J. Org. Chem.: 2008; 73 295
34. Yusubov M. S., Nemykin V. N., Zhdankin V. V. Tetrahedron: 2010; 66 5745
35. Yusubov M. S., Zagulyaeva A. A., Zhdankin V. V. Chem. Eur. J.: 2009; 15 11091
36. Dohi T., Kita Y. Chem. Commun.: 2009; 2073
37. Yusubov M. S., Zhdankin V. V. Mendeleev Commun.: 2010; 20 185
38. Richardson R. D., Wirth T. Angew. Chem. Int. Ed.: 2006; 45 4402; Angew. Chem. 2006, 118, 4510
39. Yu C., Jiang Y., Liu B., Hu L. Tetrahedron Lett.: 2001; 42 1449
40. Hernandez E., Velez J. M., Vlaar C. P. Tetrahedron Lett.: 2007; 48 8972
41. Moriarty R. M., Prakash I., Musallam H. A. Tetrahedron Lett.: 1984; 25 5867
42. Daum S. J. Tetrahedron Lett.: 1984; 25 4725
43. Zefirov N. S., Caple R., Palyulin V. A., Berglund B., Tykvinskii R., Zhdankin V. V., Kozmin A. S. Bull. Acad. Sci. USSR Div. Chem. Sci.: 1988; 37 1289
44. Prakash O., Tanwar M. P. Bull. Chem. Soc. Jpn.: 1995; 68 1168
45. Moriarty R. M., Prakash O., Duncan M. P., Vaid R. K., Rani N. J. Chem. Res., Synop.: 1996; 432
46. Moriarty R. M., Enache L. A., Zhao L., Gilardi R., Mattson M. V., Prakash O. J. Med. Chem.: 1998; 41 468
47. Varma R. S., Kumar D. Synthesis: 1999; 1288
48. Yusubov M. S., Zholobova G. A. Russ. J. Org. Chem.: 2001; 37 1179
49. Juhász L., Szilágyi L., Antus S., Visy J., Zsila F., Simonyi M. Tetrahedron: 2002; 58 4261