Stereoselective Oxidative Rearrangement of Disubstituted Unactivated Alkenes Using Hypervalent Iodine(III) Reagent
Chandra Bhan Pandey, Tazeen Azaz, Ram Subhawan Verma, Monika Mishra, Jawahar L. Jat, Bhoopendra Tiwari
Abstract
The stereoselective oxidative rearrangement of disubstituted unactivated olefins has been achieved using a hypervalent iodine(III) reagent. The aryl group undergoes 1,2-migration to give tert-α-arylated aldehydes (as acetals). The preparation of these aldehydes/acetals, especially containing a tert-benzylic stereocenter, has remained challenging. This migration-based method provides a complementary approach over the known α-substitution-based methods for accessing this class of molecules.
Topics & Concepts
Hypervalent moleculeChemistryStereocenterReagentStereoselectivityIodineArylAllylic rearrangementOxidative phosphorylationOrganic chemistryCombinatorial chemistryMedicinal chemistryAlkylCatalysisEnantioselective synthesisBiochemistryOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions