Hybrid Catalysts for Enantioselective Photo-Phosphoric Acid Catalysis

Rolka, Alessa; Archipowa, Nataliya; Kutta, Roger Jan; Koenig, Burkhard; Toste, F. Dean

doi:10.1021/acs.joc.3c00191

Cited by 6 publications

(3 citation statements)

References 75 publications

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“…Compared to other catalytic systems, [41,49] these bifunctional catalysts demonstrated potential in enantioselective energy transfer catalysis and photoredox catalysis. (Scheme 44) [52]…”

Section: The Enantioselective Synthesis With No Extraneous Photocatalystmentioning

confidence: 99%

Asymmetric Catalytic Synthesis by Synergistic Chiral Phosphoric Acid Photoredox Catalyzed Reactions

Liu

Cao

2023

Adv Synth Catal

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Chiral phosphoric acid (CPA) has been established as a cornerstone in chemical synthesis reactions for over five decades, owing to its distinctive molecular structure and remarkable catalytic effect. However, in recent years, a revolutionary approach to asymmetric synthesis has emerged, utilizing photocatalytic excitation of molecules to generate free radicals, effectively surpassing the limitations of classical organic synthesis methodologies.A prominent and significant area of research has been dedicated to the investigation of chiral phosphoric acid synergistic photocatalysis for enantioselective chemical synthesis. This unique catalytic system encompasses a bifunctional hydrogen‐bonding catalyst, enabling simultaneous interactions between radical intermediates and substrates. The review paper focuses on the application and progress of this catalytic system in asymmetric synthesis throughout the past decade.

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“…Compared to other catalytic systems, [41,49] these bifunctional catalysts demonstrated potential in enantioselective energy transfer catalysis and photoredox catalysis. (Scheme 44) [52]…”

Section: The Enantioselective Synthesis With No Extraneous Photocatalystmentioning

confidence: 99%

Asymmetric Catalytic Synthesis by Synergistic Chiral Phosphoric Acid Photoredox Catalyzed Reactions

Liu

Cao

2023

Adv Synth Catal

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“…Very recently, Toste and König group designed a bifunctional photo-organocatalyst by combining donor-acceptor type cyanoarene photocatalysts with a chiral phosphoric acid. [49] In order to test their proof of concept and the efficiency of their catalytic system, they have performed previously reported [2 + 2]-cycloaddition that goes via energy transfer pathway also it relies upon chiral phosphoric acid for inducing chirality and substrate activation by a discrete photocatalyst. [50] With 5 mol % of PBA-2 at room temperature the desired product was obtained in 70 % yield and 35 % ee with dr of 1 : 1.3 in slight preference for trans-trans product.…”

Section: Miscellaneous Reactionmentioning

confidence: 99%

Synergistic Dual Photoredox and Chiral Hydrogen Bonding Catalysis: Recent Advances

Selvakumar

2023

Asian J Org Chem

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In the last two decades, chiral hydrogen bonding catalysis has been enormously utilized to trigger several valuable synthetic transformations. Similarly, modern day radical chemistry has witnessed the potency of visible light photoredox catalysis to generate radicals via single electron transfer pathway. Recently, their cooperative effect has proved to be a key strategy to access many elegant transformations that are only feasible under the synergistic action of these two catalytic systems. This dual catalytic system demonstrates high efficiency for introducing molecular complexity in an enantioselective fashion. In this mini review, we have compiled the most recent development of this dual catalytic system that surfaced in the last three years with particular attention paid to the mechanistic details and its substrate scope. We hope that this mini review will provide readers with a brief overview of the advancement and application of photoredox catalysts and chiral hydrogen bond donors for synergistic dual catalytic reactions.

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“…Quinolines with axial chirality and central chirality are an important class of compounds in pharmaceuticals and biologically active compounds, 5 b ,9 and the catalyst-controlled synthesis of chiral quinolines has attracted significant attention over the last decade. 7,10 For instance, a quinoline-based biaryl HIV integrase inhibitor showed high potential, and the balance between potency and metabolic stability is tuned by the functional groups on C3 and C4 positions of quinoline. 11–13 Despite expectations placed on axially chiral 3-arylquinolines and their analogues as a key structure in chemistry, their applications are rare because the reported synthetic routes are limited.…”

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confidence: 99%

Enantioselective synthesis of 3-(N-indolyl)quinolines containing axial and central chiralities

Yamanomoto,

Yamamoto,

Yoshida

et al. 2024

Chem. Commun.

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Hybrid Catalysts for Enantioselective Photo-Phosphoric Acid Catalysis

Cited by 6 publications

References 75 publications

Asymmetric Catalytic Synthesis by Synergistic Chiral Phosphoric Acid Photoredox Catalyzed Reactions

Asymmetric Catalytic Synthesis by Synergistic Chiral Phosphoric Acid Photoredox Catalyzed Reactions

Synergistic Dual Photoredox and Chiral Hydrogen Bonding Catalysis: Recent Advances

Enantioselective synthesis of 3-(N-indolyl)quinolines containing axial and central chiralities

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