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Synfacts 2008(7): 0716-0716  
DOI: 10.1055/s-2008-1078459
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Oxidative Dearomatization of Naphthols with Organoiodine(III)

Contributor(s): Mark Lautens, Valentina Aureggi
T. Dohi, A. Maruyama, N. Takenaga, K. Senami, Y. Minamitsuji, H. Fujioka, S. B. Caemmerer, Y. Kita*
Osaka University, Japan
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Publication History

Publication Date:
20 June 2008 (online)

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Significance

The development of a new chiral hypervalent iodine(III) reagent for the enantioselective oxidative dearomatization of phenols is reported. The corresponding ortho-spirolactones are obtained in good yields (up to 86%) and enantio­selectivities (up to 86% ee). This work represents one of the best asymmetric transformations in the field of hypervalent iodine-mediated reactions.