Asymmetric Hydroxylative Phenol Dearomatization through In Situ Generation of Iodanes from Chiral Iodoarenes and m-CPBA

Authors

  • Stéphane Quideau Prof.,

    1. Université de Bordeaux, Institut des Sciences Moléculaires (CNRS UMR 5255), Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex (France), Fax: (+33) 5-4000-2215
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  • Gildas Lyvinec Dr.,

    1. Université de Bordeaux, Institut des Sciences Moléculaires (CNRS UMR 5255), Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex (France), Fax: (+33) 5-4000-2215
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  • Mélanie Marguerit,

    1. Université de Bordeaux, Institut des Sciences Moléculaires (CNRS UMR 5255), Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex (France), Fax: (+33) 5-4000-2215
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  • Katell Bathany,

    1. Université de Bordeaux, Institut des Sciences Moléculaires (CNRS UMR 5255), Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex (France), Fax: (+33) 5-4000-2215
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  • Aurélie Ozanne-Beaudenon Dr.,

    1. Université de Bordeaux, Institut des Sciences Moléculaires (CNRS UMR 5255), Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex (France), Fax: (+33) 5-4000-2215
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  • Thierry Buffeteau Dr.,

    1. Université de Bordeaux, Institut des Sciences Moléculaires (CNRS UMR 5255), Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex (France), Fax: (+33) 5-4000-2215
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  • Dominique Cavagnat Dr.,

    1. Université de Bordeaux, Institut des Sciences Moléculaires (CNRS UMR 5255), Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex (France), Fax: (+33) 5-4000-2215
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  • Alain Chénedé Dr.

    1. Simafex, 17230 Marans (France)
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  • We thank Simafex, the Association Nationale de la Recherche Technique (CIFRE Grants No. 457/2005 & 301/2002), and the Institut Universitaire de France for their financial support. m-CPBA=meta-chloroperoxybenzoic acid.

Abstract

′I′ is all the hype: A twofold excess of iodoarene in the title reaction leads to ortho-quinols in good yields, whereas organocatalytic versions of this reaction enable subsequent epoxidation in a regio- and diastereoselective fashion. Chiral iodobiarenes led to enantioselectivities up to 50 % ee. m-CPBA=meta-chloroperoxybenzoic acid.

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