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Synfacts 2010(3): 0357-0357
DOI: 10.1055/s-0029-1219412
DOI: 10.1055/s-0029-1219412
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of 4-Hydroxytetralones via a Cascade Stetter-Aldol Reaction
F.-G. Sun, X.-L. Huang, S. Ye
Institute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. Of China
Further Information
Publication History
Publication Date:
18 February 2010 (online)
Significance
A cascade Stetter-aldol reaction of phthalaldehyde and Michael acceptors catalyzed by N-heterocyclic carbenes derived from thiazolium salts is reported. In general aryl(vinyl)ketones and heteroaryl(vinyl)ketones are good Michael acceptors for this reaction, whereas vinylketones with a substitution in α- or β-position did not react. The resulting trans-4-hydroxytetralones could be smoothly transformed to the corresponding naphthol and naphthalenediol derivative by dehydration and Oppenauer oxidation.