Chiral phosphoric acid-catalyzed asymmetric dearomatization reactions

Chemical Society Reviews, Journal Year: 2019, Volume and Issue: 49(1), P. 286 - 300

Published: Dec. 12, 2019

We summarize in this review the recent development of chiral phosphoric acid (CPA)-catalyzed asymmetric dearomatization reactions.

Language: Английский

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Advances in Catalytic Asymmetric Dearomatization

ACS Central Science, Journal Year: 2021, Volume and Issue: 7(3), P. 432 - 444

Published: Feb. 22, 2021

Asymmetric catalysis has been recognized as the most enabling strategy for accessing chiral molecules in enantioenriched forms. Catalytic asymmetric dearomatization is an emerging and dynamic research subject catalysis, which received considerable attention recent years. The direct transformations from readily available aromatic feedstocks to structurally diverse three-dimensional polycyclic make catalytic reactions of broad interest both organic synthesis medicinal chemistry. However, inherent difficulty disruption aromaticity demands a large energy input during process, might be incompatible with conditions generally required by catalysis. In this Outlook, we will discuss representative strategies examples various compounds try convince readers that overcoming above obstacles, could advance chemical sciences many respects.

Language: Английский

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Recent Advances in the Enantioselective Synthesis of Chiral Amines via Transition Metal-Catalyzed Asymmetric Hydrogenation

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(1), P. 269 - 339

Published: Oct. 22, 2021

Chiral amines are key structural motifs present in a wide variety of natural products, drugs, and other biologically active compounds. During the past decade, significant advances have been made with respect to enantioselective synthesis chiral amines, many them based on catalytic asymmetric hydrogenation (AH). The review covers use AH bearing stereogenic center either α, β, or γ position nitrogen atom, reported from 2010 2020. Therefore, we provide an overview recent imines, enamides, enamines, allyl N-heteroaromatic

Language: Английский

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Selective Arene Hydrogenation for Direct Access to Saturated Carbo‐ and Heterocycles

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(31), P. 10460 - 10476

Published: Jan. 31, 2019

Arene hydrogenation provides direct access to saturated carbo- and heterocycles thus its strategic application may be used shorten synthetic routes. This powerful transformation is widely applied in industry expected facilitate major breakthroughs the sciences. The ability overcome aromaticity while controlling diastereo-, enantio-, chemoselectivity central use of preparation complex molecules. In general, multisubstituted arenes yields predominantly cis isomer. Enantiocontrol imparted by chiral auxiliaries, Brønsted acids, or transition-metal catalysts. Recent studies have demonstrated that highly chemoselective transformations are possible. Such methods underlying strategies reviewed herein, with an emphasis on synthetically useful examples employ readily available

Language: Английский

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Chiral Tridentate Ligands in Transition Metal-Catalyzed Asymmetric Hydrogenation

Chemical Reviews, Journal Year: 2021, Volume and Issue: 121(13), P. 7530 - 7567

Published: May 20, 2021

Asymmetric hydrogenation (AH) of double bonds has been one the most effective methods for preparation chiral molecules and synthesis important building blocks. In past 60 years, noble metals with bidentate ligands have shown marvelous reactivity enantioselectivity in asymmetric a series prochiral substrates. recent developing tridentate played an increasingly role AH. With modular frameworks variety functionalities on side arms, ligand complexes enable both reactivities stereoselectivities. Although great achievements made metal catalysts since 1990s, design earth abundant still high demand. This review summarizes development homogeneous hydrogenation. The philosophy reaction mechanisms are highlighted discussed as well.

Language: Английский

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Recent Advances in Homogeneous Catalysts for the Asymmetric Hydrogenation of Heteroarenes

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(23), P. 13834 - 13851

Published: Nov. 12, 2020

The asymmetric hydrogenation of heteroarenes has recently emerged as an effective strategy for the direct access to enantioenriched, saturated heterocycles. Although several homogeneous catalyst systems have been extensively developed with high levels chemo- and stereoselectivity, development mild conditions that allow efficient stereoselective a broad range substrates remains challenge. This Perspective highlights recent advances in catalysis heteroarene inspiration further catalysts, addresses underdeveloped areas limitations current technology.

Language: Английский

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Shaping Molecular Landscapes: Recent Advances, Opportunities, and Challenges in Dearomatization

Chem, Journal Year: 2020, Volume and Issue: 6(7), P. 1589 - 1603

Published: July 1, 2020

Language: Английский

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Silica-supported Fe/Fe–O nanoparticles for the catalytic hydrogenation of nitriles to amines in the presence of aluminium additives

Nature Catalysis, Journal Year: 2021, Volume and Issue: 5(1), P. 20 - 29

Published: Dec. 30, 2021

Abstract The hydrogenation of nitriles to amines represents an important and frequently used industrial process due the broad applicability resulting products in chemistry life sciences. Despite existing portfolio catalysts reported for nitriles, development iron-based heterogeneous this is still a challenge. Here, we show that impregnation pyrolysis iron(II) acetate on commercial silica produces reusable Fe/Fe–O@SiO 2 catalyst with well-defined structure comprising fayalite phase at Si–Fe interface α-Fe nanoparticles, covered by ultrathin amorphous iron(III) oxide layer, growing from matrix. These Fe/Fe–O core–shell presence catalytic amounts aluminium additives, promote all kinds including structurally challenging functionally diverse aromatic, heterocyclic, aliphatic fatty produce primary under scalable industrially viable conditions.

Language: Английский

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Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(3), P. 1122 - 1246

Published: Jan. 2, 2024

Dearomatization reactions have become fundamental chemical transformations in organic synthesis since they allow for the generation of three-dimensional complexity from two-dimensional precursors, bridging arene feedstocks with alicyclic structures. When those processes are applied to pyridines, quinolines, and isoquinolines, partially or fully saturated nitrogen heterocycles formed, which among most significant structural components pharmaceuticals natural products. The inherent challenge lies low reactivity heteroaromatic substrates, makes dearomatization process thermodynamically unfavorable. Usually, connecting event irreversible formation a strong C–C, C–H, C–heteroatom bond compensates energy required disrupt aromaticity. This aromaticity breakup normally results 1,2- 1,4-functionalization heterocycle. Moreover, combination these subsequent tandem stepwise protocols allows multiple heterocycle functionalizations, giving access complex molecular skeletons. aim this review, covers period 2016 2022, is update state art nucleophilic dearomatizations showing extraordinary ability dearomative methodology indicating their limitations future trends.

Language: Английский

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Asymmetric arene hydrogenation: towards sustainability and application

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(15), P. 4996 - 5012

Published: Jan. 1, 2023

This review summarises the state-of-the-art in transition-metal catalysed asymmetric hydrogenation of (hetero)arenes and highlights recent advances with a special focus on sustainability while also addressing its shortcomings.

Language: Английский

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