On the phenyliodine(III)-bis(trifluoroacetate)-mediated olefin amidohydroxylation reaction

European Journal of Organic Chemistry

Volumn , Issue 3, 2007, Pages 437-444

  Tellitu, Imanol ^a   Urrejola, Andrea ^a   Serna, Sonia ^b   Moreno, Isabel ^a   Herrero, M Teresa ^a   Domínguez, Esther ^a   SanMartin, Raul ^a   Correa, Arkaitz ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSITY OF ALCALÁ   (Spain)

Author keywords

Cyclization; Hypervalent iodine; N acylnitrenium; PIFA; Pyrrolidines

Indexed keywords

EID: 33846446683     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600782     Document Type: Article

References (58)

1. O. Mitsunobu, Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: Oxford, 1991, vol. 6, p. 65-101.
2. a) K. Marouka, H. Yamamoto, Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: Oxford, 1991, vol. 6, p. 763-793;
3. b) T. Shioiri, Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: Oxford, 1991, vol. 6, p. 795-828.
4. See, for example: a) J. Du Bois, C. S. Tomooka, J. Hong, E. M. Carreira, J. Am. Chem. Soc. 1997, 119, 3179-3180;
5. b) C. G. Espino, J. D. Bois, Angew. Chem. Int. Ed. 2001, 40, 598-599.
6. M. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579-1594.
7. See, for example: a) A. Varvoglis, Chem. Soc. Rev. 1981, 10, 377-407;
8. b) R. M. Moriarty, R. K. Vaid, Synthesis 1990, 431-447;
9. c) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178;
10. d) A. Varvoglis, S. Spyroudis, Synlett 1998, 221-232;
11. e) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523-2584;
12. f) P. J. Stang, J. Org. Chem. 2003, 68, 2997-3008;
13. g) T. Wirth, Ed. Top. Curr. Chem. 2003, 224, 1-264;
14. h) H. Tohma, Y. Kita, Adv. Synth. Catal. 2004, 346, 111-124;
15. i) R. M. Moriarty, J. Org. Chem. 2005, 70, 2893-2903;
16. j) T. Wirth, Angew. Chem. Int. Ed. 2005, 44, 3656-3665;
17. k) U. Ladziata, V. V. Zhdankin, ARKIVOC 2006, 11, 26-58.
18. nd International Conference on Hypervalent Iodine Chemistry has been recently held in Thessaloniki (Greece).
19. a) M. T. Herrero, I. Tellitu, E. Domínguez, S. Hernández, I. Moreno, R. SanMartin, Tetrahedron 2002, 58, 8581-8589;
20. b) M. T. Herrero, I. Tellitu, E. Domínguez, I. Moreno, R. SanMartin, Tetrahedron Lett. 2002, 43, 8273-8275;
21. c) A. Correa, I. Tellitu, E. Dominguez, I. Moreno, R. SanMartin, J. Org. Chem. 2005, 70, 2256-2264.
22. Y. Kikugawa, M. Kawase, Chem. Lett. 1990, 581-582.
23. For some reviews on nitrenium intermediates, see: a) D. E. Falvey, Reactive Intermediate Chemistry (Eds.: R. A. Moss, M. S. Platz, M. Jones), Wiley-Interscience, 2004; p. 594-650;
24. b) V. G. Shubin, G. I. Borodkin, Russ. J. Org. Chem. 2005, 41, 473-504.
25. S. Serna, I. Tellitu, E. Domínguez, I. Moreno, R. SanMartin, Tetrahedron Lett. 2003, 44, 3483-3486.
26. K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, S. Barluenga, K. W. Hunt, R. Kranich, J. A. Vega, J. Am. Chem. Soc. 2002, 124, 2233-2244.
27. For a recent review on amide bond formation, see: C. A. G. N. Montalbetti, V. Falque, Tetrahedron 2005, 61, 10827-10852.
28. For the preparation and full structural characterization of amide 5g, see: M. Buswell, I. Fleming, U. Ghosh, S. Mack, M. Russell, B. P. Clark, Org. Biomol. Chem. 2004, 2, 3006-3017.
29. 2 in biaryl coupling reactions promoted by PIFA. See, for example: a) T. Takada, M. Arisawa, M. Gyoten, R. Hamda, H. Tohma, Y Kita, J. Org. Chem. 1998, 63, 7698-7706;
30. b) Y. Kita, M. Gyoten, M. Ohtsubo, H. Tohma, T. Takada, Chem. Commun. 1996, 1481-1482.
31. 2, and it also resulted in complete degradation when attempts to prepare different derivatives (O-acetylation, O-tosylation, O-benzylation, and O-silylation) were carried out.
32. 13C NMR, an additional HMBC experiment was carried out to confirm the identity of pyrrolidine 6a and, hence, to exclude the formation of 6a′.
33. Arylnitrenium intermediates are known to capture water an alcohols easily. See, for example: a) P. G. Gassman, G. A. Campbell, J. Am. Chem. Soc. 1972, 94, 3891-3896;
34. b) M. Novak, M. J. Kahley, J. Lin, S. A. Kennedy, L. A. Swanegan, J. Am. Chem. Soc. 1994, 116, 11626-11627;
35. c) M. Novak, J. Lin, J. Org. Chem. 1999, 64, 6032-6040.
36. The EPR studies of different radical cations generated by PIFA from aromatic compounds have also been carried out. See, for example: a) L. Eberson, M. P. Hartshorn, O. Persson, Acta Chem. Scand. 1995, 49, 640-644;
37. b) Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakurai, S. Oka, J. Am. Chem. Soc. 1994, 116, 3684-3691. Although highly desirable, an EPR spectrum of the reaction mixture of 5a with PIFA in trifluoroethanol was impossible to be recorded due to the high polarity of this solvent.
38. a) R. Sutcliffe, D. Griller, J. Lessard, K. U. Ingold, J. Am. Chem. Soc. 1981, 103, 624-628;
39. b) R. Sutcliffe, K. U. Ingold, J. Am. Chem. Soc. 1982, 104, 6071-6075;
40. c) Y. Miura, Y. Oyama, Y. Teki, J. Org. Chem. 2003, 68, 1225-1234, and references therein.
41. a) For the shake of clarity only PMP-substituted amides, 5a and 5c, are selected to illustrate the mechanism, which equally applies to amides 5b,d;
42. b) A direct transformation from D to G can be ruled out on the basis that it would not explain the actual necessity of an aryl-donating group at nitrogen;
43. [27]
44. For related processes, see: H. Takahata, T. Suzuki, M. Maruyama, K. Moriyama, M. Mozumi, T. Takamatsu, T. Yamazaki, Tetrahedron 1988, 44, 4777-4786.
45. a) For the synthesis of 7c and 7i, see: H. Hoberg, Y. Peres, C. Krueger, Y. H. Tsay, Angew. Chem. 1987, 99, 799-800;
46. b) For 7e, see: D. Cermak, D. Wiemer, K. Lewis, R. Hohl, Bioorg. Med. Chem. 2000, 8, 2729-2737;
47. c) For 7f, see: D. H. Kim, Z.-H. Li, S. S. Lee, J. Park, S. J. Chung, Bioorg. Med. Chem. 1998, 6, 239-249.
48. M. Mori, Y. Washioka, T. Urayama, K. Yoshiura, K. Chiba, Y. Ban, J. Org. Chem. 1983, 48, 4058-4067.
49. [12]
50. a) NOE experiments were conducted on pyrrolidine 9g to confirm an anti relative configuration between substituents at 2-and 4-positions;
51. b) Complete absence of diastereocontrol was also observed in the reaction of a related compound of type 8b (R = NHPh) under a radical process mediated by IBX. K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. Int. Ed. 2000, 39, 625-628;
52. c) Pyrrolidinone 9f has been previously prepared. It is also included here for comparative purposes: S. Serna, I. Tellitu, E. Domínguez, I. Moreno, R. SanMartin, Tetrahedron 2004, 60, 6533-6539;
53. 1H NMR spectroscopy.
54. Conversely, N-aryl-5,5-diphenyl-4-pentenamidyl radicals cyclize to yield the corresponding pyrrolidinones. See: E. Martínez II, M. Newcomb, J. Org. Chem. 2006, 71, 557-561.
55. A related process of lactonization with phenonium ion participation has been published. See: A. C. Boye, D. Meyer, C. K. Inglson, A. N. French, T. Wirth, Org. Lett. 2003, 5, 2157-2159.
56. See, for example: a) S. Nagumo, Y. Ishii, Y. Kakimoto, N. Kawahara, Tetrahedron Lett. 2002, 43, 5333-5337;
57. b) S. Nagumo, M. Ono, Y. Kakimoto, T. Furukawa, T. Hisano, M. Mizukami, N. Kawahara, H. Akita, J. Org. Chem. 2002, 67, 6618-6622.
58. C. H. Larsen, B. H. Ridgway, J. T. Shaw, K. A. Woerpel, J. Am. Chem. Soc. 1999, 121, 12208-12209.