Synthesis of imides, N-acyl vinylogous carbamates and ureas, and nitriles by oxidation of amides and amines with dess-martin periodinane

Angewandte Chemie - International Edition

Volumn 44, Issue 37, 2005, Pages 5992-5997

  Nicolaou, K C ^a,b   Mathison, Casey J N ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Carbamates; Hypervalent iodine; Imides; Nitriles; Oxidation

Indexed keywords

AMINES; IODINE; OXIDATION; SUBSTRATES; UREA;

CARBAMATES; HYPERVALENT IODINE; IMIDES; NITRILES;

SYNTHESIS (CHEMICAL);

1,1,1 TRIACETOXY 1,1 DIHYDRO 1,2 BENZIODOXOL 3(1H) ONE; 1,1,1-TRIACETOXY-1,1-DIHYDRO-1,2-BENZIODOXOL-3(1H)-ONE; AMIDE; AMINE; CARBAMIC ACID DERIVATIVE; IMIDE; IODINATED HYDROCARBON; NITRILE; UREA;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

AMIDES; AMINES; CARBAMATES; HYDROCARBONS, IODINATED; IMIDES; NITRILES; OXIDATION-REDUCTION; UREA;

EID: 25144513578     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501853     Document Type: Article

References (38)

1. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155.
2. D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277.
3. V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523, and references therein.
4. a) K. C. Nicolaou, C. J. N. Mathison, T. Montagnon, Angew. Chem. 2003, 115, 4211;
5. Angew. Chem. Int. Ed. 2003, 42, 4077;
6. b) K. C. Nicolaou, C. J. N. Mathison, T. Montagnon, J. Am. Chem. Soc. 2004, 126, 5192.
7. a) K. C. Nicolaou, P. S. Baran, R. Kranich, Y.-L. Zhong, K. Sugita, N. Zou, Angew. Chem. 2001, 113, 208;
8. Angew. Chem. Int. Ed. 2001, 40, 202;
9. b) K. C. Nicolaou, K. Sugita, P. S. Baran, Y.-L. Zhong, Angew. Chem. 2001, 113, 213;
10. Angew. Chem. Int. Ed. 2001, 40, 207;
11. c) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, K. Sugita, Angew. Chem. 2001, 113, 2203;
12. Angew. Chem. Int. Ed. 2001, 40, 2145;
13. d) K. C. Nicolaou, K. Sugita, P. S. Baran, Y.-L. Zhong, J. Am. Chem. Soc. 2002, 124, 2221.
14. a) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636;
15. Angew. Chem. Int. Ed. 2000, 39, 622;
16. b) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, K. Sugita, J. Am. Chem. Soc. 2002, 124, 2212.
17. Representative procedures highlighting the utility of imides in synthesis include the reported construction of various 3-hydroxypyrroles, 1,3,4-triazines, and multifarious enantioenriched β-substituted imides and esters: a) for 3-hydroxypyrroles, see: W. Flitsch, K. Hampel, M. Hohenhorst, Tetrahedron Lett. 1987, 28, 4395;
18. b) for 1,3,4-triazines, see, for example: N. Jagerovic, L. Hernandez-Folgado, I. Alkorta, P. Goya, M. Navarro, A. Serrano, F. Rodriguez de Fonseca, M. T. Dannert, A. Alsasua, M. Suardiaz, D. Pascual, M. I. Martin, J. Med. Chem. 2004, 47, 2939;
19. c) for β-substituted imides and esters, see: C. D. Vanderwal, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 14 724.
20. a) H. B. Maruyama, Y. Suhara, J. Suzuki-Watanabe, Y. Maeshima, N. Shimizu, M. Ogura-Hamada, H. Fujimoto, K. Takano, J. Antibiot. 1975, 28, 636;
21. b) Y. Suhara, H. B. Maruyama, Y. Kotoh, Y. Miyasaka, K. Yokose, H. Shirai, K. Takano, P. Quitt, P. Lanz, J. Antibiot. 1975, 28, 648.
22. K. Krohn, C. Franke, P. G. Jones, H.-J. Aust, S. Draeger, B. Shultz, Liebigs Ann. Chem. 1992, 789.
23. J. Thirkettle, E. Alvarez, H. Boyd, M. Brown, E. Diez, J. Hueso, S. Elson, M. Fulston, C. Gershater, M. L. Morata, P. Perez, S. Ready, J. M. Sanchez-Pulles, R. Sheridan, A. Stefanska, S. Warr, J. Antibiot. 2000, 53, 664.
24. 4-based oxidation of an acyclic amide, see: L. M. Berkowitz, P. N. Rylander, J. Am. Chem. Soc. 1958, 80, 6682;
25. 4, see: K. Tanaka, S. Yoshifuji, Y. Nitta, Chem. Pharm. Bull. 1987, 35, 364.
26. V. S. Martin, J. M. Palazon, C. M. Rodriguez in Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, West Sussex, 1995, p. 4415.
27. a) For the role of IBX as a single-electron-transfer oxidant in benzylic oxidations, see: K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, J. Am. Chem. Soc. 2001, 123, 3183;
28. b) See also: K. C. Nicolaou, T. Montagnon, P. S. Baran, Y.-L. Zhong, J. Am. Chem. Soc. 2002, 124, 2245.
29. For a discussion of the thermodynamic preference for the cis-isomer in nonpolar solvents and the possibility of cis-trans interconversion of specific N-acyl vinylogous ureas, see: E. M. Suh, Y. Kishi, J. Am. Chem. Soc. 1994, 116, 11 205.
30. a) R. E. Moore, G. Bartolini, J. Am. Chem. Soc. 1981, 103, 2491;
31. b) D. Uemura, K. Ueda, Y. Hirata, H. Naoki, T. Iwashita, Tetrahedron Lett. 1981, 22, 2781.
32. S. Koshino, H. Koshino, N. Matsuura, K. Kobinata, R. Onose, K. Isono, H. Osada, J. Antibiot. 1995, 48, 185.
33. Y. Sugie, K. A. Dekker, H. Hirai, T. Ichiba, M. Ishiguro, Y. Shiomi, A. Sugiura, L. Brennan, J. Duignan, L. H. Huang, J. Sutcliffe, Y. Kojima, J. Antibiot. 2001, 54, 1060.
34. J. Schroer, M. Sanner, J.-L. Reymond, R. A. Lerner, J. Org. Chem. 1997, 62, 3220.
35. C. Han, R. Shen, S. Su, J. A. Porco, Jr., Org. Lett. 2004, 6, 27.
36. S. S. Flack, J. D. Kilburn, Tetrahedron Lett. 1995, 36, 3409.
37. F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part B, 4th ed., Kluwer Academic/Plenum, New York, 2001, p. 965.
38. R. M. Moriarty, R. K. Vaid, M. P. Duncan, M. Ochiai, M. Inenaga, Y. Nagao, Tetrahedron Lett. 1988, 29, 6913.