Hypervalent iodine-mediated oxygenative phenol dearomatization reactions

Both λ 3- and λ 5-iodanes have proven to be useful reagents in the oxygenative dearomatization of phenols, and exploitations of their chemistry in the conception of both substrate- and reagent-controlled asymmetric variants of such a transformation of great value for natural product synthesis have s...

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Bibliographic Details
Published in:Tetrahedron 2010-07, Vol.66 (31), p.5908-5917
Main Authors: Pouységu, Laurent, Sylla, Tahiri, Garnier, Tony, Rojas, Luis B., Charris, Jaime, Deffieux, Denis, Quideau, Stéphane
Format: Article
Language:English
Subjects:
Asymmetric synthesis
Cyclohexadienones
Demethylation
Hypervalent iodine
Phenol dearomatization
Quinol
Quinone monoketal
SIBX
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Summary:Both λ 3- and λ 5-iodanes have proven to be useful reagents in the oxygenative dearomatization of phenols, and exploitations of their chemistry in the conception of both substrate- and reagent-controlled asymmetric variants of such a transformation of great value for natural product synthesis have shown evident signs of success. Moreover, the use of stabilized IBX (i.e., SIBX) in our methodology for O-demethylation of 2-methoxyphenols, which relies on the same key oxygenating dearomatization event, is reported here to be much more efficacious than that of IBX itself in the chemoselective one-step conversion of homovanillyl alcohol into hydroxytyrosol, and bergenin into norbergenin. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.05.078