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Catalytic Asymmetric Umpolung Tandem Reactions of Hemiacetals via Dinuclear Zinc Cooperative Catalysis.

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The umpolung activity of hemiacetals serving as α-carbon nucleophiles has been reported via dinuclear zinc cooperative catalysis. This umpolung strategy has been applied to catalytic asymmetric tandem reactions of 1-tosylindoline-2,3-diols… Click to show full abstract

The umpolung activity of hemiacetals serving as α-carbon nucleophiles has been reported via dinuclear zinc cooperative catalysis. This umpolung strategy has been applied to catalytic asymmetric tandem reactions of 1-tosylindoline-2,3-diols with β,γ-unsaturated-α-keto compounds, providing a broad series of structurally diverse tetrahydrofuran spirooxindoles and dihydrofurans, respectively. In addition, products could be transformed to quinazoline and quinoline derivatives.

Keywords: dinuclear zinc; tandem reactions; cooperative catalysis; via dinuclear; zinc cooperative; catalytic asymmetric

Journal Title: Organic letters
Year Published: 2022

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