Evolution in heterodonor P-N, P-S and P-O chiral ligands for preparing efficient catalysts for asymmetric catalysis. From design to applications

Coordination Chemistry Reviews, Год журнала: 2021, Номер 446, С. 214120 - 214120

Опубликована: Июль 19, 2021

The success of phosphine-oxazoline ligands (PHOX) inspired the progress in P-oxazoline ligand families by modifying either backbone, electronic and/or steric properties phosphine group or exchanging to a phosphinite phosphite group. In this respect, structures chiral have become more diverse and new very efficient emerged, which improved catalytic performance some asymmetric transformations, with an increased versatility, both range reactions substrates/reagents. addition, most are synthesized from easily accessible amino alcohols, maintaining short synthetic route developed for PHOX ligands. New been replacing oxazoline functionality several other N-donor groups, e.g. imidazole, thiazole, oxazole, pyridine, etc., O- S-groups. This review offers critical overview utility these successful bidentate heterodonor P-N, P-O P-S applied metal-mediated processes. We illustrate how, through proper design, can be excellent source ligands, superior many than best C2-symmetric N,N P,P-ligands reported so far.

Язык: Английский

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Recent advances in the metal-catalyzed asymmetric alkene hydrogenation of cyclic conjugated carbonyl compounds

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(10), С. 2934 - 2953

Опубликована: Янв. 1, 2024

This review summarizes the recent advances (2016–2023) in stereoselective metal-catalyzed hydrogenation of cyclic α,β-unsaturated ketones, lactams and lactones since considerable developments were made. Where possible application these methodologies synthesis is outlined.

Язык: Английский

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Photochemical Deracemization of 3‐Substituted Oxindoles

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(30)

Опубликована: Май 22, 2023

Abstract Racemic 3‐substituted oxindoles were successfully converted into enantiomerically pure or enriched material (up to 99 % ee ) upon irradiation at λ =366 nm in the presence of a chiral benzophenone catalyst (10 mol %). The photochemical deracemization process allows predictable editing stereogenic center carbon atom C3. Light energy compensates for associated loss entropy and enables decoupling potentially reversible reactions, i.e. hydrogen transfer (photochemical) from (thermal) carbonyl group catalyst. major enantiomer is continuously several catalytic cycles. obtained shown be valuable intermediates further transformations, which proceeded with complete retention center.

Язык: Английский

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Chiral bisphosphine Ph-BPE ligand: a rising star in asymmetric synthesis

Chemical Society Reviews, Год журнала: 2024, Номер 53(13), С. 6735 - 6778

Опубликована: Янв. 1, 2024

The review summarizes the increasing applications of chiral bisphosphine ligand Ph-BPE in catalytic asymmetric reactions past twenty years.

Язык: Английский

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Robust, scalable, and highly selective spirocyclic catalysts for industrial hydroformylation and isomerization-hydroformylation

Science Advances, Год журнала: 2024, Номер 10(29)

Опубликована: Июль 17, 2024

Hydroformylation (HF) or isomerization-hydroformylation (ISO-HF) represents the most direct and practical route for producing aldehydes on an industrial scale. To resolve issues of low activity, linear/branched (

Язык: Английский

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Recent Advances in Asymmetric Hydrogenation Catalysis Utilizing Spiro and Other Rigid C-Stereogenic Phosphine Ligands

The Journal of Organic Chemistry, Год журнала: 2021, Номер 87(4), С. 1898 - 1924

Опубликована: Сен. 27, 2021

Transition-metal-catalyzed asymmetric reactions have been a powerful tool in organic synthesis for many years. The design of chiral ligands with the right configuration is fundamental to induce high regio- and stereoselectivity catalytic achieve turnover numbers yields. A challenge control prochiral centers similar electronic properties steric environment within same molecule. Over last 10 years, range novel rigid C-stereogenic phosphine has developed successfully applied various types transformations. Many these are di-, tri-, or multidentate nature. purpose this Perspective highlight recent synthetic achievements (since 2010) spiro-phosphines other phosphines discuss some mechanistic aspects reactions.

Язык: Английский

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An Overview of Hydrogen Production from Renewable Sources and Its Main Applications

ChemistrySelect, Год журнала: 2024, Номер 9(35)

Опубликована: Сен. 12, 2024

Abstract There is a misconception that sustainability only related to greenhouse gas emissions into the atmosphere, and this risk which planet exposed. Sustainability multidimensional concept must advance simoutaneously on several fronts, such as urgent need increase energy, clean water, air, food, mobility, health, poverty reduction. All problems of these multi‐dimensions are aggravated by continuous growth world population, mainly in economic socio‐environmental issues. However, biggest challenge supply energy from renewable sources, all other dimensions depend policy decisions. The consumption fossil fuels has supplied current demand approximately 87 %. Still, there predictions depletion, effects caused environment production gases bring significant losses. In review, we will address most common methods for hydrogen production, well its main technological applications organic synthesis generation.

Язык: Английский

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Green synthesis of novel cyclopentapyridines: One‐pot multicomponent reactions of vinilydene Meldrum's acid

Journal of Heterocyclic Chemistry, Год журнала: 2024, Номер 61(9), С. 1379 - 1386

Опубликована: Июнь 22, 2024

Abstract This study focused on the investigation of synthesizing new derivatives cyclopentapyridines with high yields employing multicomponent reaction that involved vinilydene Meldrum's acid, ethyl 2‐amino‐4‐dioxo‐4‐arylbutanoates, hydrazonoyl chlorides, and activated acetylenic compounds. The was conducted in water at room temperature, resulting synthesis Also, synthesized dimethyl acetylenedicarboxylate performed temperature which produced other cyclopentapyridine by elimination N 2 . advantages this technology encompass rapid response times, product yields, facile separation via uncomplicated procedures.

Язык: Английский

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Catalytic Asymmetric Syntheses of 3-Monosubstituted Oxindoles

Synthesis, Год журнала: 2024, Номер unknown

Опубликована: Июль 18, 2024

Abstract Chiral 3-monosubstituted oxindoles are privileged structural motifs in a variety of natural products and synthetic pharmaceuticals. However, catalytic asymmetric syntheses these remain challenging, mainly because the ease racemization tertiary stereocenter through enolization. In this short review, methods for preparation chiral summarized from perspective four different strategies, including Michael addition, carbenoid-mediated C–H insertion, decarboxylative protonation, indole oxidation. 1 Introduction 2 Asymmetric Addition 3 Carbenoid-Mediated Insertion 4 Decarboxylative Protonation 5 Indole Oxidation 6 Others 7 Conclusion

Язык: Английский

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Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines

Molecules, Год журнала: 2021, Номер 26(4), С. 857 - 857

Опубликована: Фев. 6, 2021

Chiral 2-oxazolines are valuable building blocks and famous ligands for asymmetric catalysis. The most common synthesis involves the reaction of an amino alcohol with a carboxylic acid. In this paper, efficient has been achieved via stereospecific isomerization 3-amido-2-phenyl azetidines. reactions were studied in presence both Brønsted Lewis acids, Cu(OTf)2 was found to be effective.

Язык: Английский

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