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Synthetic aspects of the oxidative amidation of phenols.

TitleSynthetic aspects of the oxidative amidation of phenols.
Publication TypeJournal Article
Year of Publication2010
AuthorsLiang, H, Ciufolini, MA
JournalTetrahedron
Volume66
Pagination5884 - 5892
Date Published2010///
ISBN Number0040-4020
Keywordsreview oxidative amidation phenol
Abstract

A review. The oxidative amidation of phenols effects the conversion of appropriately substituted phenols into 4-amidodienones (para-oxidative amidation’) or 2-amidodienones (ortho-oxidative amidation’) by the action of hypervalent iodine reagents. The reagent, (diacetoxyiodo)benzene (DIB’) is esp. effective in these transformations. This paper focuses on techniques for the desymmetrization of the dienones thus obtained, leading to the stereocontrolled creation of N-substituted spiro carbons. The methodol. creates new opportunities in alkaloid synthesis, as apparent from a no. of examples. [on SciFinder(R)]