Asymmetric phase-transfer catalysis

Lee, Hyo-Jun; Maruoka, Keiji

doi:10.1038/s41570-024-00642-x

Nat Rev Chem

2024

DOI: 10.1038/s41570-024-00642-x

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Asymmetric phase-transfer catalysis

Hyo-Jun Lee,

Keiji Maruoka

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2024

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Cited by 2 publications

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Enantioselective Synthesis of Chiral Acyclic Nitriles Containing α-All-Carbon Quaternary Stereocenters via Synergistic Palladium and Phase-Transfer Catalysis

Guo,

Dong,

Wang

et al. 2024

ACS Catal.

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Herein, we present a practical strategy for the asymmetric synthesis of chiral acyclic nitriles featuring α-all-carbon quaternary stereocenters, utilizing synergistic palladium and phasetransfer catalysis from allyl 2-cyanoacetates under mild conditions. This approach offers an efficient and reliable method for the in situ generation of tertiary α-cyano carbanions through intramolecular palladium-catalyzed decarboxylative allylic alkylation. Additionally, it enables highly enantioselective control of simple nitriles via ionpairing interactions with chiral phase-transfer catalysts. The synthetic utility of this method is further demonstrated by its scalability to gram-scale synthesis and its subsequent transformation into a variety of chiral functionalized compounds containing acyclic all-carbon quaternary stereocenters.

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Enantioselective Synthesis of Chiral Acyclic Nitriles Containing α-All-Carbon Quaternary Stereocenters via Synergistic Palladium and Phase-Transfer Catalysis

Guo,

Dong,

Wang

et al. 2024

ACS Catal.

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Effects of Hydrogen Bonding Solvation by Diverse Fluorinated Bulky Alcohols on the Reaction Rate and Selectivity in Crown Ether Mediated Nucleophilic Fluorination in an Aprotic Solvent

Ávila,

de Almeida,

Valle

et al. 2024

ACS Org. Inorg. Au

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Asymmetric phase-transfer catalysis

Cited by 2 publications

References 189 publications

Enantioselective Synthesis of Chiral Acyclic Nitriles Containing α-All-Carbon Quaternary Stereocenters via Synergistic Palladium and Phase-Transfer Catalysis

Enantioselective Synthesis of Chiral Acyclic Nitriles Containing α-All-Carbon Quaternary Stereocenters via Synergistic Palladium and Phase-Transfer Catalysis

Effects of Hydrogen Bonding Solvation by Diverse Fluorinated Bulky Alcohols on the Reaction Rate and Selectivity in Crown Ether Mediated Nucleophilic Fluorination in an Aprotic Solvent

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