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Title

N-Heterocyclic Carbene-Catalyzed Monoacylation of 1,4-Naphthoquinones with Aldehydes

AuthorsMolina, María Teresa ; Navarro, Cristina ; Moreno, Ana ; Csákÿ, Aurelio G.
KeywordsNaphthoquinones
Juglone
Selective acylation
NHC
Carbenes
Hydroacylation
hydroquinones
Conjugate addition of aldehydes
Issue Date25-Nov-2009
PublisherAmerican Chemical Society
CitationJ. Org. Chem. Article ASAP
AbstractThe NHC-catalyzed conjugate hydroacylation of 1,4-naphthoquinones allows for the synthesis of monoacylated 1,4-dihydroxynaphthalene derivatives. These targets, difficult to prepare selectively by standard protocols, represent important intermediates in the elaboration of highly substituted 1,4-naphthoquinone derivatives, which constitute relevant pharmaceutical scaffolds. High regioselectivity has been observed in the hydroacylation reaction when starting from nonsymmetrical quinones.
Publisher version (URL)http://pubs.acs.org/doi/pdf/10.1021/jo902235h
URIhttp://hdl.handle.net/10261/19142
DOI10.1021/jo902235h
ISSN0022-3263
Appears in Collections:(IQM) Artículos
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