Synthetic aspects of the oxidative amidation of phenols.

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)]