American Chemical Society
jo902376t_si_001.cif (16.03 kB)

Diastereoselective Synthesis of 4-Hydroxytetralones via a Cascade Stetter−Aldol Reaction Catalyzed by N-Heterocyclic Carbenes

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posted on 2010-01-01, 00:00 authored by Fang-Gang Sun, Xue-Liang Huang, Song Ye
A cascade Stetter−aldol reaction of phthalaldehyde and Michael acceptors catalyzed by N-heterocyclic carbenes was developed. The corresponding 3-substituted-4-hydroxytetralones were obtained in moderate to good yields with good trans-selectivities. On the contrary, the separated Stetter reaction followed by aldol reaction gave 3-substituted-4-hydroxytetralones with good cis-selectivity. Oxidation or dehydration of the resulted 4-hydroxytetralone gave the corresponding naphthalenediol or naphthol derivative, respectively, in good yield.