The hamburger-shape photocatalyst: thioxanthone-based chiral [2.2]paracyclophane for enantioselective visible-light photocatalysis of 3-methylquinoxalin-2(1H)-one and styrenes

Review Chemistry, Multidisciplinary

Planar Chirality: A Mine for Catalysis and Structure Discovery

Rosa Lopez et al.

Summary: This Minireview highlights the limited but significant catalytic methods for the generation of planar chirality in strained molecules, and serves as an inspiration for the development of new unconventional procedures in the future.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Review Chemistry, Multidisciplinary

Enantioselective Photochemical Reactions Enabled by Triplet Energy Transfer

Johannes Grosskopf et al.

Summary: This review provides a comprehensive survey on enantioselective photochemical reactions achieved through triplet sensitization. It is shown that highly selective enantioselective photochemical reactions can be achieved by using appropriate chiral sensitizers or a dual catalytic approach.

CHEMICAL REVIEWS (2022)

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Article Chemistry, Organic

Intramolecular, Visible-Light-Mediated Aza Paterno-Buchi Reactions of Unactivated Alkenes

Dominique E. Blackmun et al.

Summary: Azetidines are of interest in medicinal chemistry due to their favorable properties, such as increased resistance to oxidative metabolism and lower lipophilicity. The recent development of [2 + 2] reactions has expanded the methods for azetidine synthesis, but further development is needed to access more complex structures.

ORGANIC LETTERS (2022)

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Article Chemistry, Multidisciplinary

Photochemical Deracemization of Chiral Alkenes via Triplet Energy Transfer

Thilo Kratz et al.

Summary: This study describes a visible-light-mediated, enantioselective approach for the synthesis of axially chiral alkenes. By selectively transferring triplet energy from a racemic mixture, a major alkene enantiomer is formed. A small catalyst loading ensures consistently high selectivities and yields.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Organic

Stereoselective Cyclization Cascade of Dihydroquinoxalinones by Visible-Light Photocatalysis: Access to the Polycyclic Quinoxalin-2(1H)-ones

Raviramanujayya Tammisetti et al.

Summary: The stereoselective visible-light photo catalysis of dihydroquinoxalinone derivatives via cyclization has efficiently formed polycyclic ring structures, with the formation of multiple bonds and high stereoselectivity.

ORGANIC LETTERS (2022)

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Article Chemistry, Multidisciplinary

Photochemical Strategies Enable the Synthesis of Tunable Azetidine-Based Energetic Materials

Katie A. Rykaczewski et al.

Summary: In this work, a scalable synthesis method for various azetidine compounds with different properties was developed, and their potential applications in the field of high-energy materials were explored. The synthesized compounds, prepared through a visible-light-mediated reaction, exhibited excellent performance and physical properties, making them promising candidates for novel solid melt-castable explosive materials and liquid propellant plasticizers. This study demonstrates the feasibility of the visible-light synthesis method and highlights the influence of stereochemistry on the physical properties of azetidine-based energetics.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Organic

Photocatalytic Azetidine Synthesis by Aerobic Dehydrogenative [2+2] Cycloadditions of Amines with Alkenes

Malte Brasholz et al.

Summary: This paper reports a photocatalytic dehydrogenative [2 + 2] cycloaddition reaction for the synthesis of functionalized azetidines. The reaction involves the aerobic oxidation of amino acid derivatives as the amines and various alkenes, leading to high selectivity and yield of the desired products.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

Enantioselective [2+2] photocycloaddition of quinolone using a C1-symmetric chiral phosphoric acid as a visible-light photocatalyst

Ryukichi Takagi et al.

Summary: In this study, an enantioselective intra- and intermolecular [2 + 2] photocycloaddition of quinolone using a C-1-symmetric chiral phosphoric acid as a visible-light photocatalyst was developed. The thioxanthone chromophore on the phosphoric acid played a crucial role in both phototransformation and enantioselectivity.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Enantioselective, Visible Light Mediated Aza Paterno-Buchi Reactions of Quinoxalinones

Xinyao Li et al.

Summary: 3-Substituted quinoxalin-2(1H)-ones and various aryl-substituted or tethered olefins can undergo an enantioselective aza Paterno-Buchi reaction upon irradiation with a chiral sensitizer at lambda=420 nm. The absolute and relative configuration of the products were elucidated by X-ray crystallography, suggesting triplet energy transfer in a hydrogen-bonded complex between the imine substrate and the catalyst. Preliminary experiments also explored intramolecular cycloaddition and alternative reaction modes of quinoxalinones.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Organic

Kinetic Resolution of [2.2]Paracyclophane-Derived Cyclic N-Sulfonylimines via Palladium-Catalyzed Addition of Arylboronic Acids

Yang Zhao et al.

Summary: A facile method was developed for kinetic resolution of [2.2]paracyclophane-derived cyclic N-sulfonylimines based on palladium-catalyzed addition of arylboronic acids, producing two kinds of planar chiral [2.2]paracyclophane derivatives with excellent diastereoselectivities and up to 99% of enantioselectivities, along with high selectivity factors up to 128.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Applied

Multigram-Scale Kinetic Resolution of 4-Acetyl[2.2]Paracyclophane via Ru-Catalyzed Enantioselective Hydrogenation: Accessing [2.2]Paracyclophanes with Planar and Central Chirality

Christoph Zippel et al.

Summary: A kinetic resolution method was developed to obtain enantiomerically pure PCP derivatives through ruthenium-catalyzed enantioselective hydrogenation, providing important intermediates for the synthesis of chiral materials and catalysts.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Article Chemistry, Organic

Synthesis of bis(benzoxazole) frameworks chiralized by planar chiral [2.2]Paracyclophane

Emrah Polat et al.

Summary: A new class of chiral bis(benzoxazole) compounds was synthesized in this study, with enantiomeric enrichment achieved through the Horeau principle in the synthesis route. The chiralization of the achiral bis(benzoxazole) framework was achieved using a planar chiral [2.2]paracyclophane moiety.

TETRAHEDRON LETTERS (2021)

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Article Chemistry, Organic

Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane

David Weinzierl et al.

Summary: This study presents a method for the kinetic resolution of racemic 4-hydroxy[2.2]paracyclophane through a chiral isothiourea-catalyzed acylation reaction, which allows for a synthetically useful s-factor of 20 and provides a novel entry to obtain this interesting planar chiral motive in an enantioenriched manner.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

[2.2]Paracyclophane-Based Isothiourea-Catalyzed Highly Enantioselective α-Fluorination of Carboxylic Acids

Shiru Yuan et al.

Summary: In this study, planar chiral [2.2]paracyclophane-based isothiourea catalysts were synthesized in a few simple steps with high yields. These catalysts showed highly efficient catalytic enantioselective fluorination of carboxylic acids, providing a broad range of optically active alpha-fluoroesters in high yield and excellent enantioselectivity.

ORGANIC LETTERS (2021)

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Article Chemistry, Medicinal

Enantiopure planar chiral [2.2]paracyclophanes: Synthesis and applications in asymmetric organocatalysis

Simon Felder et al.

Summary: This research introduces the significance of enantiopure planar chiral [2.2]paracyclophanes in synthetic strategies, physicochemical properties, and application fields, highlighting methods for preparing optically active pCps and new synthetic possibilities. It also explores the potential and prospects of using pCps in asymmetric organocatalysis.

CHIRALITY (2021)

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Article Chemistry, Organic

Nickel-Catalyzed Asymmetric Hydrogenation for Kinetic Resolution of [2.2]Paracyclophane-Derived Cyclic N-Sulfonylimines

Yang Zhao et al.

Summary: Nickel-catalyzed asymmetric hydrogenation was successfully utilized for the kinetic resolution of cyclic N-sulfonylimines derived from [2.2]paracyclophane. High selectivity factors were observed, leading to good yields and high levels of enantiopurity in the recovered materials and hydrogenation products, which are valuable synthetic intermediates for planar chiral [2.2]paracyclophane-based compounds.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Enantioselective [2+2] Photocycloaddition via Iminium Ions: Catalysis by a Sensitizing Chiral Bronsted Acid

Franziska Pecho et al.

Summary: N,O-Acetals derived from alpha,beta-unsaturated beta-aryl substituted aldehydes and (1-aminocyclohexyl)methanol underwent a catalytic enantioselective [2 + 2] photocycloaddition to a variety of olefins with high yield and enantioselectivity under visible light irradiation using a chiral phosphoric acid as the catalyst. The formation of an iminium ion, the role of thioxanthone moieties, and the efficient enantioface differentiation were confirmed through NMR studies.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Multidisciplinary

Syntheses of new chiral chimeric photo-organocatalysts

Jiyaun Lyu et al.

Summary: A new family of chiral chimeric photo-organocatalysts derived from phosphoric acid was synthesized and characterized, followed by evaluation of their ability to catalyse an asymmetric tandem electrophilic beta-amination of enecarbamates.

RSC ADVANCES (2021)

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Review Chemistry, Organic

Thioxanthone: a powerful photocatalyst for organic reactions

Nikolaos F. Nikitas et al.

Summary: Photoorganocatalysis is recognized as an important aspect of photochemistry and catalysis in organic chemistry, with aromatic ketones playing a significant role. Thioxanthone (TX) stands out for its unique properties in photochemistry, with high triplet energy and long triplet lifetime, making it effective in merger reactions with metal complexes. This review discusses the photophysical properties of TX and its applications in various photochemical reactions, particularly in polymerization and organic transformations.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Review Chemistry, Multidisciplinary

Regioselective Functionalization of [2.2]Paracyclophanes: Recent Synthetic Progress and Perspectives

Zahid Hassan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light-Mediated Cycloadditions

Franziska Pecho et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

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Article Chemistry, Multidisciplinary

Photochemical Deracemization of Allenes and Subsequent Chirality Transfer

Manuel Plaza et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Review Chemistry, Multidisciplinary

Catalytic Enantioselective Radical Transformations Enabled by Visible Light

Debajyoti Saha

CHEMISTRY-AN ASIAN JOURNAL (2020)

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Article Chemistry, Organic

Visible-Light-Mediated Enantioselective Photoreactions of 3-Alkylquinolones with 4-O-Tethered Alkenes and Allenes

Xinyao Li et al.

ORGANIC LETTERS (2020)

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Review Chemistry, Organic

Recent developments in enantioselective photocatalysis

Callum Prentice et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Organic

Preparation of Chiral Photosensitive Organocatalysts and Their Application for the Enantioselective Synthesis of 1,2-Diamines

Jiyuan Lyu et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Review Chemistry, Multidisciplinary

Visible light photocatalysis - from racemic to asymmetric activation strategies

Thomas Rigotti et al.

CHEMICAL COMMUNICATIONS (2020)

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Review Chemistry, Organic

Cooperative photoredox and chiral hydrogen-bonding catalysis

Yanli Yin et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

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Review Chemistry, Multidisciplinary

Synthesis of azetidines by aza Paterno-Buchi reactions

Alistair D. Richardson et al.

CHEMICAL SCIENCE (2020)

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Review Chemistry, Organic

Enantioselective synthesis enabled by visible light photocatalysis

Bor-Cherng Hong

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

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Article Chemistry, Organic

Highly Enantioselective Asymmetric Transfer Hydrogenation: A Practical and Scalable Method To Efficiently Access Planar Chiral [2.2]Paracyclophanes

Marie-Leonie Delcourt et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Organic

Design of Planar Chiral Phosphoric Acids with a [2.2]Paracyclophanyl Backbone as Organocatalysts for the Highly Enantioselective Aza-Friedel-Crafts Reaction

En Xie et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Organic

Lactam Hydrogen Bonds as Control Elements in Enantioselective Transition-Metal-Catalyzed and Photochemical Reactions

Finn Burg et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Organic

Direct Transformation of Nitroalkanes to Nitriles Enabled by Visible-Light Photoredox Catalysis and a Domino Reaction Process

Yu-Hsun Li et al.

ORGANIC LETTERS (2019)

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Article Multidisciplinary Sciences

Functionalized azetidines via visible light-enabled aza Paterno-Buchi reactions

Marc R. Becker et al.

NATURE COMMUNICATIONS (2019)

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Article Chemistry, Multidisciplinary

Enantioselective Visible-Light-Mediated Formation of 3-Cyclopropylquinolones by Triplet-Sensitized Deracemization

Andreas Troester et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Review Chemistry, Organic

Advances in asymmetric visible-light photocatalysis, 2015-2019

Chunhui Jiang et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

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Review Chemistry, Organic

Photoorganocatalysis, small organic molecules and light in the service of organic synthesis: the awakening of a sleeping giant

Ioanna K. Sideri et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

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Article Chemistry, Organic

Development of Planar Chiral lodoarenes Based on [2.2]Paracyclophane and Their Application in Catalytic Enantioselective Fluorination of beta-Ketoesters

Yang Wang et al.

ORGANIC LETTERS (2018)

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Article Chemistry, Physical

Highly Enantioselective Desymmetrization of Centrosymmetric pseudo-para-Diformyl[2.2]paracyclophane via Asymmetric Transfer Hydrogenation

Marie-Leonie Delcourt et al.

ACS CATALYSIS (2018)

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Article Chemistry, Physical

A Bifunctional Photoaminocatalyst for the Alkylation of Aldehydes: Design, Analysis, and Mechanistic Studies

Thomas Rigotti et al.

ACS CATALYSIS (2018)

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Review Chemistry, Multidisciplinary

Planar chiral [2.2]paracyclophanes: from synthetic curiosity to applications in asymmetric synthesis and materials

Zahid Hassan et al.

CHEMICAL SOCIETY REVIEWS (2018)

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Article Multidisciplinary Sciences

Catalytic deracemization of chiral allenes by sensitized excitation with visible light

Alena Hoelzl-Hobmeier et al.

NATURE (2018)

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Article Chemistry, Applied

Efficient and Scalable Kinetic Resolution of Racemic 4-Formyl-[2.2]paracyclophane via Asymmetric Transfer Hydrogenation

Marie-Leonie Delcourt et al.

ADVANCED SYNTHESIS & CATALYSIS (2016)

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Article Chemistry, Multidisciplinary

Enantioselective Intermolecular [2+2] Photocycloaddition Reactions of 2(1H)-Quinolones Induced by Visible Light Irradiation

Andreas Troester et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Article Chemistry, Organic

Kinetic Resolution of a Planar-Chiral [2.2]Paracyclophane Derivative by Helical-Peptide-Catalyzed Michael Addition of Nitromethane

Kengo Akagawa et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2015)

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Article Optics

Fluorescence quenching of boronic acid derivatives by aniline in alcohols - A Negative deviation from Stern-Volmer equation

H. S. Geethanjali et al.

JOURNAL OF LUMINESCENCE (2015)

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Article Chemistry, Organic

A New Approach to Nitrones through Cascade Reaction of Nitro Compounds Enabled by Visible Light Photoredox Catalysis

Cheng-Wei Lin et al.

ORGANIC LETTERS (2015)

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Article Chemistry, Multidisciplinary

A Chiral Thioxanthone as an Organocatalyst for Enantioselective [2+2] Photocycloaddition Reactions Induced by Visible Light**

Rafael Alonso et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

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Article Chemistry, Multidisciplinary

Planar Chiral Tetrasubstituted [2.2]Paracyclophane: Optical Resolution and Functionalization

Yasuhiro Morisaki et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Article Chemistry, Multidisciplinary

Planar chiral [2.2] paracyclophane-based bis(thiourea) catalyst: application to asymmetric Henry reaction

Shinji Kitagaki et al.

CHEMICAL COMMUNICATIONS (2013)

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Article Chemistry, Organic

Sequential Asymmetric Catalysis in Michael-Michael-Michael-Aldol Reactions: Merging Organocatalysis with Photoredox Catalysis in a One-Pot Enantioselective Synthesis of Highly Functionalized Decalines Bearing a Quaternary Carbon Stereocenter

Bor-Cherng Hong et al.

ORGANIC LETTERS (2013)

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Article Chemistry, Multidisciplinary

Synthesis of a [2.2]paracyclophane based planar chiral palladacycle by a highly selective kinetic resolution/C-H activation reaction

Nathalie Dendele et al.

CHEMICAL COMMUNICATIONS (2012)

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Review Chemistry, Multidisciplinary

[2.2]Paracyclophane-Derived Planar-Chiral Hydrogen-Bond Receptors

Jakob F. Schneider et al.

ISRAEL JOURNAL OF CHEMISTRY (2012)

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Review Chemistry, Multidisciplinary

Planar Chiral Phosphines Derived from [2.2]Paracyclophane

Gareth J. Rowlands

ISRAEL JOURNAL OF CHEMISTRY (2012)

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Article Chemistry, Organic

Asymmetric β-Boration of α,β-Unsaturated N-Acyloxazolidinones by [2.2]Paracyclophane-Based Bifunctional Catalyst

Lei Zhao et al.

ORGANIC LETTERS (2012)

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Article Chemistry, Organic

Syntheses and applications of disubstituted [2.2]paracyclophanes

Olivier R. P. David

TETRAHEDRON (2012)

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Review Chemistry, Organic

[2.2]Paracyclophane Derivatives: Synthesis and Application in Catalysis

Jan Paradies

SYNTHESIS-STUTTGART (2011)

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Article Chemistry, Organic

Planar-Chiral Thioureas as Hydrogen-Bond Catalysts

Jakob F. Schneider et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2010)

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Article Chemistry, Inorganic & Nuclear

Resolution approaches to enantiomers of 4-formyl[2.2]paracyclophane

Elena V. Sergeeva et al.

TETRAHEDRON-ASYMMETRY (2010)

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Review Chemistry, Organic

Asymmetric and fused heterocycles based on [2.2]paracyclophane

Ashraf A. Aly et al.

TETRAHEDRON (2009)

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Article Chemistry, Organic

Synthesis of all possible stereoisomers of α-branched [2.2]paracyclophanylalkylamines

Dieter Enders et al.

SYNTHESIS-STUTTGART (2008)

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Article Chemistry, Inorganic & Nuclear

A simple and efficient resolution of (±)-4,12-dihydroxy[2.2]paracyclophane

B Jiang et al.

TETRAHEDRON-ASYMMETRY (2004)

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Article Biochemical Research Methods

A negative deviation from Stern-Volmer equation in fluorescence quenching

T Htun

JOURNAL OF FLUORESCENCE (2004)

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Review Chemistry, Organic

Planar and central chiral [2.2]paracyclophanes as powerful catalysts for asymmetric 1,2-addition reactions

S Bräse et al.

SYNLETT (2004)

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Article Chemistry, Organic

[2.2]Paracyclophane derivatives in asymmetric catalysis

SE Gibson et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2003)

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Article Chemistry, Organic

Improved synthesis of (±)-4,12-dihydroxy[2.2]paracyclophane and its enantiomeric resolution by enzymatic methods:: Planar chiral (R)- and (S)-phanol

DC Braddock et al.

JOURNAL OF ORGANIC CHEMISTRY (2002)

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Article Chemistry, Inorganic & Nuclear

A practical kinetic resolution of 4-acetyl[2.2]paracyclophane

P Dorizon et al.

TETRAHEDRON-ASYMMETRY (2001)

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The hamburger-shape photocatalyst: thioxanthone-based chiral [2.2]paracyclophane for enantioselective visible-light photocatalysis of 3-methylquinoxalin-2(1H)-one and styrenes

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