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Synergistic Brønsted Base/Photoredox-Catalyzed Three-Component Coupling with malonates to Synthesize δ-Hydroxy Esters and δ-Keto Esters

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Chinese Journal of Chemistry 2024年第9期42卷 957-962页

作者： Ting Li Wei Wang Ming Dong Zhije Zhang Sha Yu Zhengchu Chen Siping Wei Dong Yi Green Pharmaceutical Technology Key Laboratory of Luzhou City Central Nervous System Drug Key Laboratory of Sichuan ProvinceSchoolof PharmacySouthwestMedicalUniversityLuzhouSichuan 646000China Nuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province LuzhouSichuan 646000China

Multicomponent alkene 1,2-dicarbofunctionalizations(DCFs)have emerged as a powerful strategy to rapidly incorporate both two carbon subunits across one C-C double bond in one step for enhancing molecular complexity and *** the best of our knowledge,there is only one report on photoredox-catalyzed three-component DCFs with malonates through the radical−radical cross-coupling,while photoredox-catalyzed radical-polar crossover(RPC)-type DCFs with malonates were still ***,we describe a redox-neutral RPC-type 1,2-dialkylation of styrenes with malonates and aldehydes through the synergistic Brønsted base/photoredox catalysis *** transition-metal-free strategy provides an efficient and clean approach to a broad variety ofδ-hydroxy esters and also features exceptionally mild conditions,wide compatibility of substrate scope and functional groups,and high atomic ***,three-component 1,2-alkylacylation from the same starting materials was achieved in one-pot manner through such RPC-type coupling and subsequent two-electron oxidation process,providing a set ofδ-keto esters of interest in pharmaceutical research.

关键词： Alkene difunctionalization Photoredox catalysis malonates Radical reactions C-C coupling Synthetic methods Aldehydes Alkylation Multicomponentreactions

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Highly Enantioselective Michael Addition of Ketone to Alkylidene malonates Catalyzed by Binaphthyl Sulfonimides in Water

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Chinese Journal of Chemistry 2012年第11期30卷 2676-2680页

作者：贾胜见罗春华杜大明 School of Chemical Engineering and Environment Beijing Institute of TechnologyBeijing 100081China

Binaphthyl sulfonimides have been developed to catalyze the asymmetric Michael addition of ketone to alky- lidene malonates, affording the corresponding Michael products in good to high yields （up to 98%） with good to excellent diastereoselectivity （up to 99 ; 1 dr） and enantioselectivity （up to 92% ee） under mild conditions using environmentally benign water as the solvent.

关键词： asymmetric catalysis organocatalysis Michael addition malonates sulfonimides

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