Mechanically planar chiral rotaxanes through catalytic desymmetrization

Chem, Journal Year: 2022, Volume and Issue: 8(10), P. 2843 - 2855

Published: Sept. 8, 2022

Language: Английский

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Ligand-Enabled Sustainable Gold Catalysis

ACS Sustainable Chemistry & Engineering, Journal Year: 2022, Volume and Issue: 10(21), P. 6900 - 6918

Published: May 16, 2022

Gold catalysis has emerged as an efficient tool in the field of synthetic organic chemistry. Despite significant progress, need for high catalyst loadings mainly hampered its applicability large-scale synthesis. Recent research showcased importance ligand engineering to realize gold-catalyzed transformations at low loadings, milder reactions conditions, and greener solvents. In this perspective, we summarized reports that clearly emphasize crucial role ligands achieving highly catalysts (≤0.1 mol %) with turnover numbers frequencies. This perspective also briefly discusses challenges future potential development ppm-level gold catalysis.

Language: Английский

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Recent Developments in Enantioselective Domino Reactions. Part A: Noble Metal Catalysts

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(5), P. 620 - 681

Published: Jan. 17, 2023

Abstract This review updates the field of enantioselective domino reactions promoted by chiral catalysts derived from noble metals, including palladium, silver, rhodium, ruthenium, iridium and gold, published since beginning 2019. It illustrates how much a diversity these allow unprecedented asymmetric many types to be achieved with excellent enantioselectivity, giving direct access wide variety complex molecules. magnified image

Language: Английский

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Amino Acid-Derived Ionic Chiral Catalysts Enable Desymmetrizing Cross-Coupling to Remote Acyclic Quaternary Stereocenters

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(30), P. 16796 - 16811

Published: July 20, 2023

Synthetic application of asymmetric catalysis relies on strategic alignment bond construction to creation chirality a target molecule. Remote desymmetrization offers distinctive advantages spatial decoupling catalytic transformation and generation stereogenic element. However, such separation presents substantial difficulties for the chiral catalyst discriminate distant enantiotopic sites through reaction three or more bonds away from prochirality center. Here, we report strategy that establishes acyclic quaternary carbon stereocenters cross-coupling reactions at distal positions aryl substituents. The new class amino acid-derived ionic catalysts enables desymmetrizing (enantiotopic-group-selective) Suzuki-Miyaura reaction, Sonogashira Buchwald-Hartwig amination between diverse diarylmethane scaffolds aryl, alkynyl, coupling partners, providing rapid access enantioenriched molecules project substituents widely spaced in three-dimensional space. Experimental computational investigations reveal electrostatic steering substrates by C-terminus ligands interactions. Cooperative ion-dipole interactions catalyst's amide group potassium cation aid preorganization transmits asymmetry product. This study demonstrates it is practical achieve precise long-range stereocontrol engineering arrangements catalysts' substrate-recognizing groups metal centers.

Language: Английский

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Enantioselective merged gold/organocatalysis

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(27), P. 3607 - 3623

Published: Jan. 1, 2024

This highlight demonstrates the state of art in field enantioselective merged gold/organocatalysis by leveraging unique reactivity each catalyst.

Language: Английский

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