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Design of Efficient Chiral Bifunctional Phase-Transfer Catalysts Possessing an Amino Functionality for Asymmetric Aminations

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An efficient, chiral bifunctional phase-transfer catalyst with an intramolecular amino functionality has been designed and successfully applied to highly enantioselective amination of 3-aryloxindoles and 3-arylbenzofuran-2(3H)-ones with bis(adamantyl) azodicarboxylate. Optically active… Click to show full abstract

An efficient, chiral bifunctional phase-transfer catalyst with an intramolecular amino functionality has been designed and successfully applied to highly enantioselective amination of 3-aryloxindoles and 3-arylbenzofuran-2(3H)-ones with bis(adamantyl) azodicarboxylate. Optically active amination products were generally obtained in high yield with high enantioselectivity. The origin of stereoselectivity was explained by means of the DFT calculations.

Keywords: chiral bifunctional; phase transfer; efficient chiral; bifunctional phase; amino functionality

Journal Title: ACS Catalysis
Year Published: 2018

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