Brønsted acid-catalyzed enantioselective addition of 1,3-diones to <i>in situ</i> generated <i>N</i>-acyl ketimines
Milon M. Sadhu, Sumit Kumar Ray, Rajshekhar A. Unhale, Vinod K. Singh
Abstract
-acyl ketimines is reported for the synthesis of enantioenriched isoindolinones. Various dicarbonyl-substituted isoindolinones bearing a quaternary carbon stereocenter were synthesized with excellent yields (up to 98%) and moderate to high enantioselectivities (up to 95% ee), and most of them possess a fluorine atom at the reactive center. Furthermore, the synthetic utility of the protocol has been demonstrated by the debenzoylation of the product.
Topics & Concepts
StereocenterChemistryEnantioselective synthesisBrønsted–Lowry acid–base theoryCatalysisQuaternary carbonCarbon atomOrganic chemistryFluorineCarbon fibersOrganocatalysisMedicinal chemistryCombinatorial chemistryRing (chemistry)Materials scienceComposite materialComposite numberSynthesis and pharmacology of benzodiazepine derivativesSynthetic Organic Chemistry MethodsAsymmetric Synthesis and Catalysis