Organophosphites: An Addition to the Arsenal of Organocatalysts

Article Chemistry, Multidisciplinary

NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy-Breslow Intermediates

Terence Wu et al.

Summary: This study demonstrates that pyridinium ions can undergo NHC addition and intramolecular C-C bond formation through a deoxy-Breslow intermediate, presenting a new pathway for catalytic reactions of non-aldehyde substrates.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Physical

Access to Planar Chiral Ferrocenes via N-Heterocyclic Carbene-Catalyzed Enantioselective Desymmetrization Reactions

Xiaokang Lv et al.

Summary: Ferrocene-derived dicarbaldehydes with pro-chiral planes can be desymmetrized under the catalysis of chiral Nheterocyclic carbene organic catalysts, resulting in enantiomerically enriched planar chiral ferrocene products. The reaction selectively activates and reacts with one aldehyde moiety while leaving the other untouched. The obtained products show potential applications as catalysts in chemical synthesis and for antimicrobial activities in pesticide development.

ACS CATALYSIS (2022)

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Article Chemistry, Multidisciplinary

Aroyl Fluorides as Bifunctional Reagents for Dearomatizing Fluoroaroylation of Benzofurans

Xiaoye Yu et al.

Summary: In this study, a method using aroyl fluorides as bifunctional reagents for the dearomatization of dihydrobenzofurans was reported. The reaction proceeds through cooperative NHC/photoredox catalysis, resulting in the formation of 2,3-difunctionalized dihydrobenzofuran compounds with moderate to high yield and high diastereoselectivity. The reaction also exhibits broad substrate scope and high functional group compatibility.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Review Chemistry, Multidisciplinary

Single-electron carbene catalysis in redox processes

Anna Bay et al.

Summary: Chemists have used the polarity reversal reactivity of N-heterocyclic carbenes (NHCs) to build key chemical bonds, and their redox properties enable the synthesis of stable radical species. This has greatly contributed to the field of synthetic chemistry and the revival of radical chemistry.

TRENDS IN CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

N-Heterocyclic carbene (NHC)-catalyzed oxidation of unactivated aldimines to amides via imine umpolung under aerobic conditions

Jakkula Ramarao et al.

Summary: In this study, we present a novel method for converting imines to amides using an eco-friendly approach. The method involves an NHC-catalyzed oxidation of unactivated aldimines and utilizes molecular oxygen and dimethyl carbonate as the sole oxidant and solvent, respectively, under mild reaction conditions. The developed method demonstrates a broad substrate scope, high yields, and scalability, making it practical for large-scale synthesis.

RSC ADVANCES (2022)

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Review Chemistry, Multidisciplinary

Generation and Reactivity of C(1)-Ammonium Enolates by Using Isothiourea Catalysis

Calum McLaughlin et al.

Summary: Ammonium enolates are powerful synthetic intermediates generated catalytically using isothiourea Lewis base organocatalysts, and have been applied in selective alpha-functionalisation reactions with various precursors. Their utility in intra- and intermolecular C-C and C-X bond forming processes with electrophiles is showcased using different catalyst turnover approaches.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Article Chemistry, Multidisciplinary

Critical Assessment of the Reducing Ability of Breslow-type Derivatives and Implications for Carbene-Catalyzed Radical Reactions**

Ludivine Delfau et al.

Summary: This study reported the synthesis of acyl azolium salts from various types of carbenes and the generation of their corresponding radicals and enolates, revealing the role of additives in the redox behavior of these compounds and correcting misconceptions about radical transformations of aldehyde derivatives. The reducing ability of enolates derived from certain carbenes was found to be underestimated, and catalytic intermediates were shown to transfer electrons efficiently at room temperature. Enol derivatives of certain carbenes were identified as powerful reducing agents.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Asymmetric Carbene-Catalyzed Oxidation of Functionalized Aldimines as 1,4-Dipoles

Guanjie Wang et al.

Summary: Functionalized aldimines have been used as new 1,4-dipole precursors in carbene catalysis, leading to enantiodivergent organocatalysis for the synthesis of both (R)- and (S)- enantiomers of compounds with quaternary carbon centers. The key factors for controlling enantioselectivity were found to be hydrogen bond C-H...F interactions between catalyst and substrate. These new 1,4-dipoles can also react with isatin and its imines under carbene catalysis, producing spiro oxindoles with excellent enantiomeric ratios.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Carbene-Catalyzed Activation of Remote Nitrogen Atoms of (Benz)imidazole-Derived Aldimines for Enantioselective Synthesis of Heterocycles

Xing Yang et al.

Summary: This new mode of carbene-catalyzed reaction involves the activation of a nitrogen atom in a triaza-diene intermediate, leading to highly enantioselective reactions with activated ketones. The reaction pathway is supported by mechanistic studies and preliminary density function theory calculations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Organic

Norrish type II reactions of acyl azolium salts

Andreas Mavroskoufis et al.

Summary: The photochemical reactivity of acyl azolium salts derived from aliphatic carboxylic acids was investigated, showing Norris type II elimination reactions and Norris-Yang cyclization under UVA light irradiation. These results demonstrate the influence of NHCs on the absorption properties and photochemical reactivity of carbonyl groups during a catalytic cycle.

TETRAHEDRON (2021)

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Review Chemistry, Multidisciplinary

C(sp2)-H functionalization of aldimines and related compounds: advances and prospects

Alexey A. Akulov et al.

Summary: This review systematically examines the approaches to direct C(sp(2))-H bond functionalization of azomethine derivatives, evaluating the scope of various transformations and discussing the prospects of applying this strategy in the multistep synthesis of valuable compounds for medicinal chemistry, materials science, and other related fields.

RUSSIAN CHEMICAL REVIEWS (2021)

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Review Chemistry, Organic

Cyanide Anions as Nucleophilic Catalysts in Organic Synthesis

David Kieslich et al.

Summary: The nucleophilic addition of a cyanide anion to a carbonyl group serves as the basis for several cyanide-catalyzed organic reactions, with examples including the benzoin condensation and the Michael-Stetter reaction. Apart from the fundamental reactions, variants like the silyl-benzoin coupling and cyanide-catalyzed heterocyclic syntheses are also covered.

SYNTHESIS-STUTTGART (2021)

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Review Chemistry, Multidisciplinary

Carbene-Catalyzed Asymmetric Construction of Atropisomers

Runjiang Song et al.

Summary: NHC catalysis has shown great potential in accessing atropisomeric molecules, offering unique reaction modes for asymmetric synthesis. The progress in this field includes kinetic resolutions, asymmetric desymmetrizations, and the conversion of central-to-axial chirality, highlighting the promising future applications of NHC-based organic catalysis in preparing challenging atropisomeric compounds.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones

Anna Bay et al.

Summary: This study reports the light-driven synthesis of aliphatic and alpha-amino ketones using single-electron NHC operators. Computational and experimental results show that the reactivity of the key radical intermediate depends on the substrate and can be modulated through steric and electronic parameters of the NHC. This methodology is showcased in the direct late-stage functionalization of amino acids and pharmaceutical compounds, highlighting the utility of single-electron NHC operators.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Phosphite mediated asymmetric N to C migration for the synthesis of chiral heterocycles from primary amines

Soniya Rani et al.

Summary: The phosphite mediated stereoretentive C-H alkylation of N-alkylpyridinium salts derived from chiral primary amines was achieved through activation with a nucleophilic phosphite catalyst, base mediated [1,2] aza-Wittig rearrangement, and subsequent alkyl migration. Experimental and theoretical investigations supported an unprecedented rearrangement-rearomatization sequence, leading to efficient access to tertiary and quaternary stereogenic centers in pyridine systems. This method also allowed for a catalytic enantioselective version using racemic starting material and chiral phosphite catalyst.

CHEMICAL SCIENCE (2021)

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Review Chemistry, Multidisciplinary

Tale of the Breslow intermediate, a central player in N-heterocyclic carbene organocatalysis: then and now

Monika Pareek et al.

Summary: N-Heterocyclic carbenes (NHCs) are popular organocatalysts known for their umpolung reactivity on aldehydes and ketones. Recent research has focused on gaining insights into the formation and characterization of Breslow intermediates, which play a central role in organocatalytic reactions.

CHEMICAL SCIENCE (2021)

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Review Chemistry, Organic

α,β-Unsaturated acyl ammonium species as reactive intermediates in organocatalysis: an update

Jacqueline Bitai et al.

Summary: Alpha, beta-unsaturated acyl ammonium species are versatile intermediates used in various transformations, especially in those catalyzed by chiral Lewis bases, allowing for rapid generation of molecular complexity with precise stereochemical control. This review highlights recent advances in the generation and application of these intermediates, focusing on mechanistic insights and observed selectivities, while also discussing current challenges and potential future developments in this field.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

N-Heterocyclic Carbene Catalyzed Photoenolization/Diels-Alder Reaction of Acid Fluorides

Andreas Mavroskoufis et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids

Anna V. Bay et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Organic

Chlorosilane-Catalyzed Coupling of Hydrogen Phosphine Oxides with Acyl Chlorides Generating Acylphosphine Oxides

Jian-Qiu Zhang et al.

ORGANIC LETTERS (2020)

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Review Chemistry, Multidisciplinary

Recent advances in N-heterocyclic carbene-based radical catalysis

Takuya Ishii et al.

CHEMICAL SCIENCE (2020)

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Article Chemistry, Multidisciplinary

N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes

Takuya Ishii et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Physical

N-Heterocyclic Carbene-Catalyzed Umpolung of Imines for the Enantioselective Synthesis of Dihydroquinoxalines

Tamal Kanti Das et al.

ACS CATALYSIS (2019)

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Article Chemistry, Organic

Chiral Nitroarenes as Enantioselective Single-Electron-Transfer Oxidants for Carbene-Catalyzed Radical Reactions

Hongling Wang et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Multidisciplinary

Phosphite-Catalyzed C-H Allylation of Azaarenes via an Enantioselective [2,3]-Aza-Wittig Rearrangement

Abdul Motaleb et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Multidisciplinary

Enantioselective N-Heterocyclic Carbene Catalysis that Exploits Imine Umpolung

Jared E. M. Fernando et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Review Biochemistry & Molecular Biology

Synthesis and Reactions of α-Hydroxyphosphonates

Zita Radai et al.

MOLECULES (2018)

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Article Chemistry, Organic

An organocatalyst bound -aminoalkyl radical intermediate for controlled aerobic oxidation of iminium ions

Abdul Motaleb et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

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Article Chemistry, Organic

Synthetic Approach to Benzocyclobutenones Using Visible Light and a Phosphonate Auxiliary

Takaaki Yano et al.

ORGANIC LETTERS (2018)

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Article Chemistry, Organic

A removable functional group strategy for regiodivergent Wittig rearrangement products

Md Nirshad Alam et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

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Article Chemistry, Organic

Synthesis of 3-Formylbenzenesulfonyl Chloride Derivativesv

Xuefei Bao et al.

SYNTHESIS-STUTTGART (2017)

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Article Chemistry, Multidisciplinary

N-Heterocyclic carbene-catalyzed oxidative [3+2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate

Xiang-Yu Chen et al.

CHEMICAL SCIENCE (2017)

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Article Chemistry, Multidisciplinary

N-Heterocyclic carbene (NHC)-catalysed atom economical construction of 2,3-disubstituted indoles

Battu Harish et al.

CHEMICAL COMMUNICATIONS (2017)

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Article Chemistry, Multidisciplinary

N-Heterocyclic-Carbene-Catalyzed Umpolung of Imines

Atanu Patra et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Article Chemistry, Organic

Asymmetric Organocatalytic Reductive Coupling Reactions between Benzylidene Pyruvates and Aldehydes

Matthew A. Horwitz et al.

ORGANIC LETTERS (2016)

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Article Chemistry, Multidisciplinary

N-Heterocyclic Carbene Catalyzed γ-Dihalomethylenation of Enals by Single-Electron Transfer

Wen Yang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Article Chemistry, Multidisciplinary

Enzymatic Chemoselective Aldehyde-Ketone Cross-Couplings through the Polarity Reversal of Methylacetoin

Giovanni Bernacchia et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Review Chemistry, Multidisciplinary

Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes

Darrin M. Flanigan et al.

CHEMICAL REVIEWS (2015)

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Article Chemistry, Organic

Aza-Wittig Rearrangements of N-Benzyl and N-Allyl Glycine Methyl Esters. Discovery of a Surprising Cascade Aza-Wittig Rearrangement/Hydroboration Reaction

Renata K. Everett et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

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Article Chemistry, Multidisciplinary

N-Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β-Hydroxylation of Enals

Yuexia Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Article Chemistry, Organic

Catalytic Aldol-Cyclization Cascade of 3-Isothiocyanato Oxindoles with α-Ketophosphonates for the Enantioselective Synthesis of β-Amino-α-hydroxyphosphonates

Satavisha Kayal et al.

ORGANIC LETTERS (2015)

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Article Chemistry, Multidisciplinary

Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes

Matthew A. Horwitz et al.

CHEMICAL SCIENCE (2015)

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Article Chemistry, Medicinal

Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among US FDA Approved Pharmaceuticals

Edon Vitaku et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

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Article Chemistry, Multidisciplinary

Enantioselective N-Heterocyclic Carbene-Catalyzed β-Hydroxylation of Enals Using Nitroarenes: An Atom Transfer Reaction That Proceeds via Single Electron Transfer

Nicholas A. White et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Article Chemistry, Multidisciplinary

Metallo phosphonate catalyzed benzoin couplings: the influence of the counterion

Maria Schumacher et al.

NEW JOURNAL OF CHEMISTRY (2014)

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Review Chemistry, Multidisciplinary

Recent Advances in Organocatalytic Asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman Reactions

Yin Wei et al.

CHEMICAL REVIEWS (2013)

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Article Chemistry, Organic

Bronsted Base Catalyzed [2,3]-Wittig/Phospha-Brook Tandem Rearrangement Sequence

Azusa Kondoh et al.

ORGANIC LETTERS (2013)

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Article Chemistry, Organic

Primary and secondary amine-(thio)ureas and squaramides and their applications in asymmetric organocatalysis

Michail Tsakos et al.

TETRAHEDRON (2013)

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Review Chemistry, Multidisciplinary

Catalytic Asymmetric Claisen Rearrangement of Enolphosphonates: Construction of Vicinal Tertiary and All-Carbon Quaternary Centers

Jiajing Tan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

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Article Chemistry, Multidisciplinary

Base-Catalyzed Direct Aldolization of α-Alkyl-α-Hydroxy Trialkyl Phosphonoacetates

Michael T. Corbett et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

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Review Chemistry, Multidisciplinary

Recent developments in metal catalyzed asymmetric addition of phosphorus nucleophiles

Depeng Zhao et al.

CHEMICAL SOCIETY REVIEWS (2012)

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Article Chemistry, Organic

Lithium phosphonate umpolung catalysts: Do fluoro substituents increase the catalytic activity?

Anca Gliga et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2011)

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Review Chemistry, Multidisciplinary

C-C Bond-Forming Lyases in Organic Synthesis

Margarita Brovetto et al.

CHEMICAL REVIEWS (2011)

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Article Chemistry, Organic

New Umpolung Catalysts: Reactivity and Selectivity of Terpenol-Based Lithium Phosphonates in Enantioselective Benzoin-Type Couplings

Anca Gliga et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2011)

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Article Chemistry, Organic

Lanthanum Tricyanide-Catalyzed Acyl Silane-Ketone Benzoin Additions and Kinetic Resolution of Resultant α-Silyloxyketones

James C. Tarr et al.

JOURNAL OF ORGANIC CHEMISTRY (2010)

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Article Chemistry, Organic

Catalytic Nucleophilic Glyoxylation of Aldehydes

Kimberly M. Steward et al.

ORGANIC LETTERS (2010)

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Article Chemistry, Multidisciplinary

Anion-Catalyzed Addition of γ-Silylallenyl Esters to Aldehydes: A New Entry into [3.2.1] Bicyclic Natural Products

Pradip Maity et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

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Article Chemistry, Organic

Lanthanum Tricyanide-Catalyzed Acyl Silane-Ketone Benzoin Additions

James C. Tarr et al.

ORGANIC LETTERS (2009)

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Review Chemistry, Multidisciplinary

Asymmetric aminocatalysis - Gold rush in organic chemistry

Paolo Melchiorre et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

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Article Chemistry, Multidisciplinary

Biomimetic Carbene-Catalyzed Oxidations of Aldehydes Using TEMPO

Joyram Guin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

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Article Chemistry, Organic

Overcoming the Limitations of the Morita-Baylis-Hillman Reaction: A Rapid and General Synthesis of α-Alkenyl-β′-hydroxy Thioesters

Emily Tarsis et al.

ORGANIC LETTERS (2008)

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Review Chemistry, Multidisciplinary

Chiral dialkylaminopyridine catalysts in asymmetric synthesis

Ryan P. Wurz

CHEMICAL REVIEWS (2007)

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Review Chemistry, Multidisciplinary

Recent developments in the use of catalytic asymmetric ammonium enolates in chemical synthesis

Matthew J. Gaunt et al.

CHEMICAL REVIEWS (2007)

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Review Chemistry, Multidisciplinary

Organocatalysis by N-heterocyclic, carbenes

Dieter Enders et al.

CHEMICAL REVIEWS (2007)

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Article Chemistry, Multidisciplinary

Enantioselective metallophosphite-catalyzed C-acylation of nitrones

Mary R. Garrett et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

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Article Chemistry, Multidisciplinary

Metallophosphite-catalyzed asymmetric acylation of α,β-unsaturated amides

MR Nahm et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

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Article Chemistry, Multidisciplinary

Enantioselective catalytic intramolecular cyclopropanation using modified cinchona alkaloid organocatalysts

Carin C. C. Johansson et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

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Article Chemistry, Organic

Tandem Horner-Wadsworth-Emmons olefination/claisen rearrangement/hydrolysis sequence: Remarkable acceleration in water with microwave irradiation

E Quesada et al.

SYNTHESIS-STUTTGART (2005)

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Article Chemistry, Organic

Improved solution- and solid-phase preparation of hydroxamic acids from esters

CY Ho et al.

JOURNAL OF ORGANIC CHEMISTRY (2005)

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Article Chemistry, Multidisciplinary

Mechanism and scope of the cyanide-catalyzed cross silyl benzoin reaction

LH Xin et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

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Article Chemistry, Multidisciplinary

Metallophosphite-induced nucleophilic acylation of alpha,beta-unsaturated amides: Facilitated catalysis by a diastereoselective retro [1,4] Brook rearrangement

MR Nahm et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

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Article Chemistry, Multidisciplinary

Metallophosphites as umpolung catalysts: The enantioselective cross silyl benzoin reaction

LH Xin et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

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Article Chemistry, Multidisciplinary

Enantioselective organocatalytic cyclopropanation via ammonium ylides

CD Papageorgiou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2004)

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Article Chemistry, Multidisciplinary

An intramolecular organocatalytic cyclopropanation reaction

N Bremeyer et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2004)

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Review Chemistry, Multidisciplinary

Recent advances in the Baylis-Hillman reaction and applications

D Basavaiah et al.

CHEMICAL REVIEWS (2003)

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Article Chemistry, Multidisciplinary

Kinetic control in direct alpha-silyloxy ketone synthesis: A new regiospecific catalyzed cross silyl benzoin reaction

LH Xin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2003)

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Article Chemistry, Multidisciplinary

Organic-catalyst-mediated cyclopropanation reaction

CD Papageorgiou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2003)

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Article Multidisciplinary Sciences

Crystal structure of the free radical intermediate of pyruvate:ferredoxin oxidoreductase

E Chabrière et al.

SCIENCE (2001)

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Article Chemistry, Organic

The aza-[2,3]-Wittig sigmatropic rearrangement of acyclic amines: Scope and limitations of silicon assistance

JC Anderson et al.

JOURNAL OF ORGANIC CHEMISTRY (2000)

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Review Chemistry, Multidisciplinary

Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition

BL Feringa

ACCOUNTS OF CHEMICAL RESEARCH (2000)

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Organophosphites: An Addition to the Arsenal of Organocatalysts

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