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

Geden, Joanna V.; Clark, Andrew J.; Coles, Stuart R.; Guy, Collette S.; Ghelfi, Franco; Thom, Stephen

doi:10.1016/j.tetlet.2016.06.009

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

Copper mediated cyclization of 1-substituted enamides, dienamides and trienamides: regiochemistry, indigoid formation and methyl migration-aromatization / Geden, Joanna V.; Clark, Andrew J.; Coles, Stuart R.; Guy, Collette S.; Ghelfi, Franco; Thom, Stephen. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 57:29(2016), pp. 3109-3112.

Data di pubblicazione:	2016
Titolo:	Copper mediated cyclization of 1-substituted enamides, dienamides and trienamides: regiochemistry, indigoid formation and methyl migration-aromatization
Autore/i:	Geden, Joanna V.; Clark, Andrew J.; Coles, Stuart R.; Guy, Collette S.; Ghelfi, Franco; Thom, Stephen
Autore/i UNIMORE:	Geden, Joanna V. Clark, Andrew J. Coles, Stuart R. Guy, Collette S. GHELFI, Franco Thom, Stephen mostra contributor esterni nascondi contributor esterni
Digital Object Identifier (DOI):	http://dx.doi.org/10.1016/j.tetlet.2016.06.009
Rivista:	TETRAHEDRON LETTERS
Volume:	57
Fascicolo:	29
Pagina iniziale:	3109
Pagina finale:	3112
Codice identificativo ISI:	WOS:000379630500013
Codice identificativo Scopus:	2-s2.0-84975824325
Citazione:	Copper mediated cyclization of 1-substituted enamides, dienamides and trienamides: regiochemistry, indigoid formation and methyl migration-aromatization / Geden, Joanna V.; Clark, Andrew J.; Coles, Stuart R.; Guy, Collette S.; Ghelfi, Franco; Thom, Stephen. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 57:29(2016), pp. 3109-3112.
Tipologia	Articolo su rivista

File in questo prodotto:

Non ci sono file associati a questo prodotto.

Utilizza questo identificativo per citare o creare un link a questo documento:
http://hdl.handle.net/11380/1140482

Citazioni

I documenti presenti in Iris Unimore sono rilasciati con licenza Creative Commons Attribuzione - Non commerciale - Non opere derivate 3.0 Italia, salvo diversa indicazione.
In caso di violazione di copyright, contattare Supporto Iris