A new and practical PIFA-promoted olefin amidohydroxylation: Six- versus five-membered ring formation

Tetrahedron Letters

Volumn 44, Issue 17, 2003, Pages 3483-3486

  Serna, Sonia ^a   Tellitu, Imanol ^a   Domínguez, Esther ^a   Moreno, Isabel ^a   SanMartín, Raúl ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALLYL COMPOUND; AROMATIC COMPOUND; BENZAMIDE DERIVATIVE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; IODINE DERIVATIVE; ISOQUINOLINE DERIVATIVE; PHENYLIODINE BIS(TRIFLUOROACETATE); UNCLASSIFIED DRUG; VINYL DERIVATIVE;

AMIDOHYDROXYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CYCLIZATION; HYDROLYSIS; PRECURSOR; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0037459842     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00670-1     Document Type: Article

References (31)

1. See for example: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407; (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; (c) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; (d) Varvoglis, A.; Spyroudis, S. Synlett 1998, 221-232; (e) For a very recent revision of the chemistry of hypervalent iodine compounds, see: Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584.
2. See for example: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407; (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; (c) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; (d) Varvoglis, A.; Spyroudis, S. Synlett 1998, 221-232; (e) For a very recent revision of the chemistry of hypervalent iodine compounds, see: Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584.
3. See for example: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407; (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; (c) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; (d) Varvoglis, A.; Spyroudis, S. Synlett 1998, 221-232; (e) For a very recent revision of the chemistry of hypervalent iodine compounds, see: Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584.
4. See for example: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407; (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; (c) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; (d) Varvoglis, A.; Spyroudis, S. Synlett 1998, 221-232; (e) For a very recent revision of the chemistry of hypervalent iodine compounds, see: Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584.
5. See for example: (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377-407; (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; (c) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; (d) Varvoglis, A.; Spyroudis, S. Synlett 1998, 221-232; (e) For a very recent revision of the chemistry of hypervalent iodine compounds, see: Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584.
6. (a) For a revision of the chemistry of hypervalent iodine compounds in the oxidative coupling reaction, see: Moreno, I.; Tellitu, I.; Herrero, M. T.; SanMartín, R.; Domínguez, E.; Curr. Org. Chem. 2002, 6, 1433-1452;
7. (b) For the PIFA mediated oxidative coupling reaction in the synthesis of phenanthridines, see: Moreno, I.; Tellitu, I.; Etayo, J.; Domínguez, E.; SanMartín, R. Tetrahedron 2001, 57, 5403-5411;
8. (c) For the synthesis of phenanthrenes and phenanthrenoids, see: Moreno, I.; Tellitu, I.; SanMartín, R.; Domínguez, E. Eur. J. Org. Chem. 2002, 2126-2135;
9. (d) Moreno, I.; Tellitu, I.; SanMartín, R.; Domínguez, E. Synlett 2001, 1161-1163.
10. Herrero M. T., Tellitu I., Hernández S., Domínguez E., Moreno I., SanMartín R. Tetrahedron. 58:2002;8581-8589.
11. Herrero M. T., Tellitu I., Moreno I., Domínguez E., Moreno I., SanMartín R. Tetrahedron Lett. 43:2002;8273-8275.
12. It is accepted that these reactions take place through a single-electron transfer (SET) mechanism. See: Kita Y., Tohma H., Hatanaka K., Takada T., Fujita S., Mitoh S., Sakurai H., Oka S. J. Am. Chem. Soc. 116:1994;3684-3691.
13. Kikugawa Y., Kawase M. Chem. Lett. 1990;581-582.
14. For related works on metal-assisted nitrogen atom transfer to olefins employing hypervalent iodine reagents, see: (a) Levites-Agababa, E.; Menhaji, E.; Perlson, L. N.; Rojas, C. M. Org. Lett. 2002, 4, 863-865; (b) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137-2139.
15. For related works on metal-assisted nitrogen atom transfer to olefins employing hypervalent iodine reagents, see: (a) Levites-Agababa, E.; Menhaji, E.; Perlson, L. N.; Rojas, C. M. Org. Lett. 2002, 4, 863-865; (b) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137-2139.
16. Kryska A., Skulski L. J. Chem. Res. (S). 1999;590-591.
17. For physical and spectroscopic information of the so-obtained 4,5-dimethoxy-2-iodobenzoic acid, see: Harayama T., Shibaike K. Heterocycles. 49:1998;191-195.
18. Romero has employed TFA as additive in a PIFA-mediated oxidative cyclization of a N-methoxyamide to obtain the tetrahydroquinoline skeleton with excellent results. However, the role of TFA remains unknown. See: Romero A. G., Darlington W. H., McMillan M. W. J. Org. Chem. 62:1997;6582-6587.
19. It has been proposed that the coordination of this Lewis acid with the trifluoroacetoxy ligands activates the iodine(III) reagent. See: Takada T., Arisawa M., Gyoten M., Hamada R., Tohma H., Kita Y. J. Org. Chem. 63:1998;7698-7706.
20. Data of compound 4 can be found in: Kundu N. G., Khan M. W. Tetrahedron. 56:2000;4777-4792 In all cases under study, reported in Scheme 2, heterocycles 4 and 5 were isolated from complex mixtures of non-identified compounds. Temperature selection was optimized for each case without modification of the regioselectivity of the cyclization.
21. By altering the reaction conditions, ortho-allylanilines have also been transformed regioselectively into indoles via a 5-exo-trig process (Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113-1126) and into quinolines via a 6-endo-trig cyclization mode (Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584-3585).
22. By altering the reaction conditions, ortho-allylanilines have also been transformed regioselectively into indoles via a 5-exo-trig process (Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113-1126) and into quinolines via a 6-endo-trig cyclization mode (Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584-3585).
23. Baldwin J. E. J. Chem. Soc., Chem. Commun. 1976;734-736.
24. Nicolaou K. C., Baran P. S., Zhong Y. L., Barluenga S., Hunt K. W., Kranich R., Vega J. A. J. Am. Chem. Soc. 124:2002;2233-22344.
25. 3CN solvents. See for example: (a) Kita, Y.; Takada, T.; Mihara, S.; Whelan, B. A.; Tohma, H. J. Org. Chem. 1995, 60, 7144-7148; (b) Ward, R. S.; Pelter, A.; Abd-El-Ghani, A. Tetrahedron 1996, 52, 1303-1336.
26. 3CN solvents. See for example: (a) Kita, Y.; Takada, T.; Mihara, S.; Whelan, B. A.; Tohma, H. J. Org. Chem. 1995, 60, 7144-7148; (b) Ward, R. S.; Pelter, A.; Abd-El-Ghani, A. Tetrahedron 1996, 52, 1303-1336.
27. 2OH as solvent without any activating agent.
28. 5 329.1263, found 329.1261.
29. For related mechanistic studies using IBX as the hypervalent iodine reagent, see: Nicolaou K. C., Baran P. S., Kranich R., Zhong Y.-L., Sugita K., Zou N. Angew. Chem., Int. Ed. 40:2001;202-206.
30. The putative structure of trifluoroacetyl ester V was proposed based on the close similarity between the proton NMR of the reaction mixture from 2b to 6a (prior to basification) and the ester 6b .
31. 4 504.2049, found 504.2041.