Application of peptidyl radicals into a new radical cascade leading to unsaturated γ-lactams

Journal of Organic Chemistry

Volumn 68, Issue 4, 2003, Pages 1552-1554

  Andrukiewicz, Robert ^a   Loska, Rafał ^a   Prisyahnyuk, Vladimir ^a   Staliński, Krzysztof ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

RADICAL CYCLIZATION;

CATALYST ACTIVITY; FREE RADICAL REACTIONS;

POLYCYCLIC AROMATIC HYDROCARBONS;

ALPHA AMINO ACID; AMINO ACID; DIPEPTIDE; GAMMA LACTAM DERIVATIVE; GLYCINE; RADICAL;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

AMINO ACIDS; CATALYSIS; CYCLIZATION; DIPEPTIDES; LACTAMS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 0037458968     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020602w     Document Type: Article

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11. Generally, other 1,n-H transfers are known, for example. 1,3-H transfer: Damour, D.; Barreau, M.; Dhaleine, F.; Doerfingler, G.; Vuilhorgne, M.; Mignani, S. Synlett 1996, 890-892. 1,4-H transfers: (a) Wallace, T. J.; Gritter, R. J. J. Org. Chem. 1961, 26, 5256. (b) Johnson, R. A.; Greene, F. D. J. Org. Chem. 1975, 40, 2186-2192. (c) Gilbert, B. C.; Parry, D. J.; Grossi, L. J. Chem. Soc., Faraday Trans. 1 1987, 77-83. (d) Journet, M.; Malacria, M. Tetrahedron Lett. 1992, 33, 1893-1896. 1,6-H transfers: (a) Gross, A.; Fensterbank, L.; Bogen, S.; Thouvenot, R.; Malacria, M. Tetrahedron Lett. 1997, 53, 13797-13810. (b) Nedelec, J. Y.; Lefort, D. Tetrahedron 1975, 31, 411-417. (c) Curran, D. P.; Yu, H. S.; Liu, H. T. Tetrahedron 1994, 50, 7343-7366. 1,7-H transfers: (a) Curran, D. P.; Somayajula, K. S.; Yu, H. Tetrahedron Lett. 1992, 33, 2295-2298. (b) Denenmark, D.; Winkler, T.; Waldner, A.; De Mesmaeker, A. Tetrahedron Lett. 1992, 33, 3613-3616. (c) Curran, D. P.; Xu, J.; Lazzarini, E. J. Chem. Soc., Perkin Trans. 1 1995, 3049-3059.
12. Generally, other 1,n-H transfers are known, for example. 1,3-H transfer: Damour, D.; Barreau, M.; Dhaleine, F.; Doerfingler, G.; Vuilhorgne, M.; Mignani, S. Synlett 1996, 890-892. 1,4-H transfers: (a) Wallace, T. J.; Gritter, R. J. J. Org. Chem. 1961, 26, 5256. (b) Johnson, R. A.; Greene, F. D. J. Org. Chem. 1975, 40, 2186-2192. (c) Gilbert, B. C.; Parry, D. J.; Grossi, L. J. Chem. Soc., Faraday Trans. 1 1987, 77-83. (d) Journet, M.; Malacria, M. Tetrahedron Lett. 1992, 33, 1893-1896. 1,6-H transfers: (a) Gross, A.; Fensterbank, L.; Bogen, S.; Thouvenot, R.; Malacria, M. Tetrahedron Lett. 1997, 53, 13797-13810. (b) Nedelec, J. Y.; Lefort, D. Tetrahedron 1975, 31, 411-417. (c) Curran, D. P.; Yu, H. S.; Liu, H. T. Tetrahedron 1994, 50, 7343-7366. 1,7-H transfers: (a) Curran, D. P.; Somayajula, K. S.; Yu, H. Tetrahedron Lett. 1992, 33, 2295-2298. (b) Denenmark, D.; Winkler, T.; Waldner, A.; De Mesmaeker, A. Tetrahedron Lett. 1992, 33, 3613-3616. (c) Curran, D. P.; Xu, J.; Lazzarini, E. J. Chem. Soc., Perkin Trans. 1 1995, 3049-3059.
13. Generally, other 1,n-H transfers are known, for example. 1,3-H transfer: Damour, D.; Barreau, M.; Dhaleine, F.; Doerfingler, G.; Vuilhorgne, M.; Mignani, S. Synlett 1996, 890-892. 1,4-H transfers: (a) Wallace, T. J.; Gritter, R. J. J. Org. Chem. 1961, 26, 5256. (b) Johnson, R. A.; Greene, F. D. J. Org. Chem. 1975, 40, 2186-2192. (c) Gilbert, B. C.; Parry, D. J.; Grossi, L. J. Chem. Soc., Faraday Trans. 1 1987, 77-83. (d) Journet, M.; Malacria, M. Tetrahedron Lett. 1992, 33, 1893-1896. 1,6-H transfers: (a) Gross, A.; Fensterbank, L.; Bogen, S.; Thouvenot, R.; Malacria, M. Tetrahedron Lett. 1997, 53, 13797-13810. (b) Nedelec, J. Y.; Lefort, D. Tetrahedron 1975, 31, 411-417. (c) Curran, D. P.; Yu, H. S.; Liu, H. T. Tetrahedron 1994, 50, 7343-7366. 1,7-H transfers: (a) Curran, D. P.; Somayajula, K. S.; Yu, H. Tetrahedron Lett. 1992, 33, 2295-2298. (b) Denenmark, D.; Winkler, T.; Waldner, A.; De Mesmaeker, A. Tetrahedron Lett. 1992, 33, 3613-3616. (c) Curran, D. P.; Xu, J.; Lazzarini, E. J. Chem. Soc., Perkin Trans. 1 1995, 3049-3059.
14. Generally, other 1,n-H transfers are known, for example. 1,3-H transfer: Damour, D.; Barreau, M.; Dhaleine, F.; Doerfingler, G.; Vuilhorgne, M.; Mignani, S. Synlett 1996, 890-892. 1,4-H transfers: (a) Wallace, T. J.; Gritter, R. J. J. Org. Chem. 1961, 26, 5256. (b) Johnson, R. A.; Greene, F. D. J. Org. Chem. 1975, 40, 2186-2192. (c) Gilbert, B. C.; Parry, D. J.; Grossi, L. J. Chem. Soc., Faraday Trans. 1 1987, 77-83. (d) Journet, M.; Malacria, M. Tetrahedron Lett. 1992, 33, 1893-1896. 1,6-H transfers: (a) Gross, A.; Fensterbank, L.; Bogen, S.; Thouvenot, R.; Malacria, M. Tetrahedron Lett. 1997, 53, 13797-13810. (b) Nedelec, J. Y.; Lefort, D. Tetrahedron 1975, 31, 411-417. (c) Curran, D. P.; Yu, H. S.; Liu, H. T. Tetrahedron 1994, 50, 7343-7366. 1,7-H transfers: (a) Curran, D. P.; Somayajula, K. S.; Yu, H. Tetrahedron Lett. 1992, 33, 2295-2298. (b) Denenmark, D.; Winkler, T.; Waldner, A.; De Mesmaeker, A. Tetrahedron Lett. 1992, 33, 3613-3616. (c) Curran, D. P.; Xu, J.; Lazzarini, E. J. Chem. Soc., Perkin Trans. 1 1995, 3049-3059.
15. Generally, other 1,n-H transfers are known, for example. 1,3-H transfer: Damour, D.; Barreau, M.; Dhaleine, F.; Doerfingler, G.; Vuilhorgne, M.; Mignani, S. Synlett 1996, 890-892. 1,4-H transfers: (a) Wallace, T. J.; Gritter, R. J. J. Org. Chem. 1961, 26, 5256. (b) Johnson, R. A.; Greene, F. D. J. Org. Chem. 1975, 40, 2186-2192. (c) Gilbert, B. C.; Parry, D. J.; Grossi, L. J. Chem. Soc., Faraday Trans. 1 1987, 77-83. (d) Journet, M.; Malacria, M. Tetrahedron Lett. 1992, 33, 1893-1896. 1,6-H transfers: (a) Gross, A.; Fensterbank, L.; Bogen, S.; Thouvenot, R.; Malacria, M. Tetrahedron Lett. 1997, 53, 13797-13810. (b) Nedelec, J. Y.; Lefort, D. Tetrahedron 1975, 31, 411-417. (c) Curran, D. P.; Yu, H. S.; Liu, H. T. Tetrahedron 1994, 50, 7343-7366. 1,7-H transfers: (a) Curran, D. P.; Somayajula, K. S.; Yu, H. Tetrahedron Lett. 1992, 33, 2295-2298. (b) Denenmark, D.; Winkler, T.; Waldner, A.; De Mesmaeker, A. Tetrahedron Lett. 1992, 33, 3613-3616. (c) Curran, D. P.; Xu, J.; Lazzarini, E. J. Chem. Soc., Perkin Trans. 1 1995, 3049-3059.
16. Generally, other 1,n-H transfers are known, for example. 1,3-H transfer: Damour, D.; Barreau, M.; Dhaleine, F.; Doerfingler, G.; Vuilhorgne, M.; Mignani, S. Synlett 1996, 890-892. 1,4-H transfers: (a) Wallace, T. J.; Gritter, R. J. J. Org. Chem. 1961, 26, 5256. (b) Johnson, R. A.; Greene, F. D. J. Org. Chem. 1975, 40, 2186-2192. (c) Gilbert, B. C.; Parry, D. J.; Grossi, L. J. Chem. Soc., Faraday Trans. 1 1987, 77-83. (d) Journet, M.; Malacria, M. Tetrahedron Lett. 1992, 33, 1893-1896. 1,6-H transfers: (a) Gross, A.; Fensterbank, L.; Bogen, S.; Thouvenot, R.; Malacria, M. Tetrahedron Lett. 1997, 53, 13797-13810. (b) Nedelec, J. Y.; Lefort, D. Tetrahedron 1975, 31, 411-417. (c) Curran, D. P.; Yu, H. S.; Liu, H. T. Tetrahedron 1994, 50, 7343-7366. 1,7-H transfers: (a) Curran, D. P.; Somayajula, K. S.; Yu, H. Tetrahedron Lett. 1992, 33, 2295-2298. (b) Denenmark, D.; Winkler, T.; Waldner, A.; De Mesmaeker, A. Tetrahedron Lett. 1992, 33, 3613-3616. (c) Curran, D. P.; Xu, J.; Lazzarini, E. J. Chem. Soc., Perkin Trans. 1 1995, 3049-3059.
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