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Catalytic Enantioselective Synthesis of Spirooxindoles by Oxidative Rearrangement of Indoles

Chenxiao Qian, Pengfei Li, Jianwei Sun

2020Angewandte Chemie International Edition65 citationsDOI

Abstract

Oxidative rearrangement of indoles to access oxindoles has been used as a key step in complex molecule synthesis. We report a catalytic enantioselective variant of this transformation by chiral phosphoric acid catalysis, providing rapid access to a range of enantioenriched spirooxindoles. The high enantioselectivity is controlled by dynamic kinetic resolution.

Topics & Concepts

Enantioselective synthesisCatalysisOxidative phosphorylationCombinatorial chemistryChemistryPhosphoric acidKinetic resolutionOrganic chemistryBiochemistryAsymmetric Synthesis and CatalysisOxidative Organic Chemistry ReactionsAlkaloids: synthesis and pharmacology
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