Journal of Organic Chemistry 2009-12-18

N-Heterocyclic carbene-catalyzed monoacylation of 1,4-naphthoquinones with aldehydes.

María Teresa Molina, Cristina Navarro, Ana Moreno, Aurelio G Csákÿ

Index: J. Org. Chem. 74(24) , 9573-5, (2009)

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Abstract

The 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.