title: Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents.
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.
authors.affiliation: School of Chemistry, Cardiff University, Park Place, Main Building, Cardiff, CF10 3AT, UK.
authors.forename: Florence
authors.initials: F
authors.lastname: Malmedy
authors.affiliation: School of Chemistry, Cardiff University, Park Place, Main Building, Cardiff, CF10 3AT, UK. wirth@cf.ac.uk.
authors.forename: Thomas
authors.initials: T
authors.lastname: Wirth
keywords: addition; alkenes; iodine(III); rearrangement; stereoselective synthesis