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

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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:	Date Event 20 July 2016 Published 2 June 2016 Available 1 June 2016 Accepted 20 April 2016 Submitted
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
Funder:	AstraZeneca (Firm), Charnwood Molecular Ltd, University of Warwick, Engineering and Physical Sciences Research Council (EPSRC)
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