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Copper mediated cyclization of 1-substituted enamides, dienamides and trienamides : regiochemistry, indigoid formation and methyl migration-aromatization

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Geden, Joanna V., Clark, Andrew J., Coles, Stuart R., Guy, Collete S., Ghelfi, Franco and Thom, Stephen (2016) Copper mediated cyclization of 1-substituted enamides, dienamides and trienamides : regiochemistry, indigoid formation and methyl migration-aromatization. Tetrahedron Letters, 57 . pp. 3109-3122. doi:10.1016/j.tetlet.2016.06.009 ISSN 0040-4039.

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Official URL: http://dx.doi.org/10.1016/j.tetlet.2016.06.009

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Abstract

Copper mediated cyclization of activated 1-substituted enamides occurs via a 5-endo radical-polar crossover process. Trichloroacetyl derivatives can undergo further reactions post cyclization (elimination of HCl or dimerization potentially via copper carbenoid intermediates). Reaction of α-halo trienamides derived from β-ionone furnish either β- or γ-lactams via 4-exo or 5-exo cyclizations respectively depending upon the enamide tautomer undergoing reaction. For the less reactive dichloroacetamide derivative a competing regioselective methyl migration-aromatization prior to cyclization is observed.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science, Engineering and Medicine > Science > Chemistry
Library of Congress Subject Headings (LCSH): Copper -- Experiments
Journal or Publication Title: Tetrahedron Letters
Publisher: Elsevier
ISSN: 0040-4039
Official Date: 20 July 2016
Dates:
DateEvent
20 July 2016Published
2 June 2016Available
1 June 2016Accepted
20 April 2016Submitted
Volume: 57
Page Range: pp. 3109-3122
DOI: 10.1016/j.tetlet.2016.06.009
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Restricted or Subscription Access
Date of first compliant deposit: 23 August 2016
Date of first compliant Open Access: 2 June 2017
Funder: AstraZeneca (Firm), Charnwood Molecular Ltd, University of Warwick, Engineering and Physical Sciences Research Council (EPSRC)
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