Recent years have seen an increasing interest in the use of chiral hypervalent iodide reagents/catalysts for stereoselective oxidation reactions. The low toxicity and ease of recoverability of these reagents make them attractive alternatives to transition metal-based catalysts. They also demonstrate unique modes of reactivity that are not available with other reagents. We will report our recent efforts aimed at using chiral aryl iodides in two main areas. The first concerns the design of new catalysts for performing enantioselective dearomatzation of prochiral phenols. These efforts have mostly been focused on generating enantioenriched 2,5-cyclohexadienones. The second involves performing stereoselective oxidative cyclizations on olefinic substrates. Our interests in this area have focused on the construction of medicinally relevant heterocycles and the use of unusual exogenous nucleophiles.

Chiral aryl iodide catalysts and reagents for seteroselective oxidation reactions

245th National Meeting (2013)

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