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Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents
Authors:Florence Malmedy  Prof. Dr. Thomas Wirth
Affiliation:School of Chemistry, Cardiff University, Cardiff, UK
Abstract:The first stereoselective version of an iodine(III)‐mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α‐arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid‐based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.
Keywords:addition  alkenes  iodine(III)  rearrangement  stereoselective synthesis
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