Regiochemistry of copper(I)-mediated cyclization reactions of halo-dienamides

Journal of Organic Chemistry

Volumn 72, Issue 15, 2007, Pages 5923-5926

  Clark, Andrew J ^a   Geden, Joanna V ^a   Thom, Stephen ^b   Wilson, Paul ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER HALIDE; HALO-DIENAMIDES; REGIOCHEMISTRY; TRIPYRIDYLAMINE (TPA);

AMIDES; CATALYST ACTIVITY; CYCLIZATION; HALOGEN COMPOUNDS; REACTION KINETICS;

COPPER COMPOUNDS;

ALKADIENE; AMIDE; BETA LACTAM; BRAIN AMINE; COPPER; DIENAMIDE DERIVATIVE; HALIDE; OXYGEN; TRIPYRIDYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

AMIDES; COPPER; CYCLIZATION;

EID: 34547100956     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070680p     Document Type: Article

References (18)

1. Clark, A. J. Chem. Soc. Rev. 2002, 1.
2. (a) Nagashima, H.; Ozaki, N.; Ishii, M.; Seki, K.; Washiyama, M.; Itoh, K. J. Org. Chem. 1993, 58, 464.
3. (b) Nagashima, H.; Isono, Y.; Iwamatsu, S. J. Org. Chem. 2001, 66, 315.
4. (c) Udding, J. H.; Tuijp, C. J. M.; van Zanden, M. N. A.; Hiemstra, H.; Speckamp, J. Org. Chem. 1994, 59, 1993.
5. (d) Bryans, J. S.; Chessum, N. E. A.; Huther, N.; Parsons, A. F.; Ghelfi, F. Tetrahedron 2003, 59 6221.
6. (a) Benedetti, M.; Forti, L.; Ghelfi, F.; Pagnoni, U. M.; Ronzoni, R. Tetrahedron 1997, 41, 14031.
7. (b) De Buyck, L.; Cagnoli, R.; Ghelfi, F.; Merighi, G.; Mucci, A.; Pagnoni, U. M.; Parsons, A. F. Synthesis 2004, 10, 1680.
8. (a) Clark, A. J.; De Campo, F.; Deeth, R. J.; Filik, R. P.; Gatard, S.; Hunt, N. A.; Lastécouères, D.; Thomas, G. H.; Verlac J.-B.; Wongtap H. J. Chem. Soc., Perkin Trans. 1 2000, 671.
9. (b) Clark, A. J.; Dell, C. P.; Ellard, J. M.; Hunt, N. A.; McDonagh, J. P. Tetrahedron Lett. 1999, 40, 8619.
10. (c) Clark, A. J.; Filik, R. P.; Thomas, G. H. Tetrahedron Lett. 1999, 40, 4885.
11. (a) De Campo, F.; Lastécouères, D.; Verlac J.-B. J. Chem. Soc., Chem. Commun., 1998, 2117.
12. (b) Clark, A. J.; Dell, C. P.; McDonagh, J. P. C.R. Acad. Sci. Ser IIC: Chim. 2001, 4, 575.
13. Clark, A. J.; Battle, G. M.; Bridge, A. Tetrahedron Lett. 2001, 42, 4409.
14. Ishibashi, H. Chem. Rec. 2006, 6, 23.
15. Presumably caused by oxidation of the CuCl/TPA complex to the corresponding Cu(II) peroxo complex: Chishiro, T.; Shimazaki, F.; Tani, F.; Tachi, Y.; Naruka, Y.; Karasawa, S.; Hayani, S.; Maeda, Y, Angew. Chem., Int. Ed. 2003, 42, 2788.
16. Gani, V.; Viout, P. Tetrahedron 1978, 34, 1337.
17. Cyclization onto imines: (a) Tajino, M.; Otsuka, N.; Fukuyama, T.; Matsubara, H.; Ryu, I. J. Am. Chem. Soc. 2006, 128, 7712.
18. (b) Cyclization of vinyl radicals: (c) Quirante, J.; Vila, X.; Palona, L.; Guiu, J. M.; Bonjoch, J. Tetrahedron 2007, 63, 1372.