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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
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: |
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| 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) | ||||||||||
| Adapted As: |
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