Regio- and diastereoselective access to densely functionalized ketones <i>via</i> the Boekelheide rearrangement of isoxazoline <i>N</i> -oxides
Pavel Yu. Ushakov, Sema L. Ioffe, Alexey Yu. Sukhorukov
Abstract
-oxide moiety. Subsequent deoxygenative C-H functionalization using the Boekelheide rearrangement and hydrogenolysis of the isoxazoline ring afforded α'-acyloxy-substituted aldols, which are difficult to access both by the classical aldol reaction and the "isoxazoline route". The products are formed in good to high overall yields and as single diastereomers in most cases. The synthetic use of these aldols was showcased by their smooth transformation into diastereomerically pure triols and a 2,3-diaryl-4-hydroxy-substituted tetrahydrofuran derivative, which is structurally related to cinncassin B.
Topics & Concepts
ChemistryRegioselectivityHydrogenolysisMoietyAnnulationRing (chemistry)TetrahydrofuranNitrileAldol reactionCycloadditionStereochemistryDerivative (finance)Medicinal chemistryOrganic chemistryCatalysisFinancial economicsEconomicsSolventSynthesis and Catalytic ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods