Radical cascade involving a 5-endo-trig cyclization of α-amidoyl radicals

Author:

Ishibashi Hiroyuki,Ishita Atsuko,Tamura Osamu

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference16 articles.

1. For reviews, see: Malacria, M. Chem. Rev. 1996, 96, 289–306; McCarrol, A. J.; Walton, J. C. Angew. Chem., Int. Ed. Engl. 2001, 40, 2225–2248.

2. 6-Endo-trig and 5-exo-trig selective aryl radical cyclisations of N-(o-bromobenzyl) enamides

3. 1,4-Pentadienyl-3-sulfonamides:  Frameworks for “Disfavored” Radical Cascade Cyclizations

4. 5-Endo-trigonal reactions: a disfavoured ring closure

5. For effective 5-endo-trig cyclizations of N-vinylic carbamoylmethyl radicals, see: (a) Ishibashi, H.; Nakamura, N.; Sato, T.; Takeuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725–1728; (b) Sato, T.; Nakamura, N.; Ikeda, K.; Okada, M.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1992, 2399–2407; (c) Ishibashi, H.; Higuchi, M.; Ohba, M.; Ikeda, M. Tetrahedron Lett. 1998, 39, 75–78; (d) Baker, S. R.; Parsons, A. F.; Wilson, M. Tetrahedron Lett. 1998, 39, 2815–2818; (e) Davies, D. T.; Kapur, N.; Parsons, A. F. Tetrahedron Lett. 1998, 39, 4397–4400; (f) Cassayre, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, A. Z. Tetrahedron Lett. 1998, 39, 8995–8998; (g) Cassayre, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, A. Z. Tetrahedron 1998, 54, 1029–1040; (h) Ikeda, M.; Ohtani, S.; Yamamoto, T.; Sato, T.; Ishibashi, H. J. Chem. Soc., Perkin Trans. 1 1998, 1763–1768; (i) Ikeda, M.; Ohtani, S.; Sato, T.; Ishibashi, H. Synthesis 1998, 1803–1806; (j) Clark, A. J.; Dell, C. P.; Ellard, J. M.; Hunt, N. A.; McDonagh, J. P. Tetrahedron Lett. 1999, 40, 8619–8623; (k) Cassayre, J.; Zard, S. Z. Synlett 1999, 501–503; (l) Baker, S. R.; Burton, K. I.; Parsons, A. F.; Pons, J.-F.; Wilson, M. J. Chem. Soc., Perkin Trans. 1 1999, 427–436; (m) Ikeda, M.; Hamada, M.; Yamashita, T.; Matsui, K.; Sato, T.; Ishibashi, H. J. Chem. Soc., Perkin Trans. 1 1999, 1949–1956; (n) Ishibashi, H.; Toyao, A.; Takeda, Y. Synlett 1999, 1468–1470; (o) Ishibashi, H.; Matsukida, H.; Toyao, A.; Tamura, O.; Takeda, Y. Synlett 2000, 1497–1499; (p) Toyao, A.; Chikaoka, S.; Takeda, Y.; Tamura, O.; Muraoka, O.; Tanabe, G.; Ishibashi, H. Tetrahedron Lett. 2001, 42, 1729–1732. See also references cited therein.

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