☆ 4.7 Review

Recent Developments in Enantioselective Domino Reactions. Part A: Noble Metal Catalysts

ADVANCED SYNTHESIS & CATALYSIS (2023)

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Review Chemistry, Multidisciplinary

Aromatic π-Components for Enantioselective Heck Reactions and Heck/Anion-Capture Domino Sequences

Ren-Xiao Liang et al.

Summary: Palladium-catalyzed Heck reactions and related pathways have provided efficient and direct methods for synthesizing structurally diverse heteropolycyclic molecules by extending coupling partners from classical olefins to aromatic systems. These reactions have successfully been applied to a variety of new π-coupling partners.

ACCOUNTS OF CHEMICAL RESEARCH (2022)

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Article Chemistry, Multidisciplinary

Asymmetric Auto-Tandem Palladium Catalysis for 2,4-Dienyl Carbonates: Ligand-Controlled Divergent Synthesis

Jian-Xiang Zhu et al.

Summary: This study presents the development of a new asymmetric auto-tandem catalysis process, which allows for the synthesis of diverse compounds with excellent stereocontrol. The use of chiral ligands enables the switchable diastereodivergent synthesis, demonstrating the versatility of this auto-tandem catalysis.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Organic

Copper-Catalyzed Asymmetric Hydroallylation of Vinylsilanes

Simin Wang et al.

Summary: A copper-catalyzed asymmetric hydroallylation reaction was developed for the transformation of readily available vinylsilanes with allylic phosphates in the presence of hydrosilane. The reactions can be conducted under mild conditions and provide chiral organosilanes with good to excellent enantiocontrol.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Organic

Ag-Catalyzed Asymmetric Interrupted Barton-Zard Reaction Enabling the Enantioselective Dearomatization of 2-and 3-Nitroindoles

Wei-Cheng Yuan et al.

Summary: In this study, a novel Ag-catalyzed asymmetric reaction was developed to achieve the dearomatization of nitroindoles, leading to the synthesis of a variety of optically active tetrahydropyrrolo[3,4-b]indole derivatives with high yields and enantioselectivity. The synthetic potential of this protocol was demonstrated through gram-scale reactions and versatile transformations of the product.

ORGANIC LETTERS (2022)

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Review Chemistry, Organic

Stereoselective Domino Reactions in the Synthesis of Spiro Compounds

Regina Westphal et al.

Summary: This review summarizes the latest developments in asymmetric domino reactions, with a focus on the preparation of spiro compounds. Discussions on the stereoselectivity of the transformations, reaction mechanisms, rationalization of the stereochemical outcome, and the applications of domino reactions to the synthesis of biologically active molecules and natural products are included.

SYNTHESIS-STUTTGART (2022)

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Article Chemistry, Multidisciplinary

Enantioselective difunctionalization of alkenes by a palladium-catalyzed Heck/borylation sequence

Yuanqi Wu et al.

Summary: A palladium catalyzed enantioselective Heck/borylation reaction of alkene-tethered aryl iodides was developed, providing a range of 2,3-dihydrobenzofuranyl boronic esters with high yield and excellent enantioselectivity. Asymmetric synthesis of chromane boronic ester, indane boronic ester and indoline boronic ester was also achieved.

CHEMICAL SCIENCE (2022)

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Article Chemistry, Organic

Palladium-catalyzed tandem Heck/carbonylation/aminocarbonylation en route to chiral heterocyclic α-ketoamides

Huaanzi Hu et al.

Summary: An unprecedented tandem carbonylation/aminocarbonylation reaction triggered by a palladium-catalyzed enantioselective Heck-type exocyclopalladation has been developed to deliver chiral heterocyclic alpha-ketoamides. Unique structures featuring alkyl alpha-ketoamides hybridized with indolin-2-one and 5,7-dihydro-6H-dibenzo[b,d]azepin-6-one, containing stereogenic centers, are produced in good yields with excellent enantio- and/or diastereoselectivities.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Article Chemistry, Multidisciplinary

Enantioselective synthesis of indenopyrazolopyrazolones enabled by dual directing groups-assisted and rhodium(III)-catalyzed tandem C-H alkenylation/[3+2] stepwise cycloaddition

Min Wu et al.

Summary: The (CpRh)-Rh-X(III)-catalyzed asymmetric cascade C-H coupling/intramolecular cyclization of azomethine imines with propargyl carbonates has been developed, leading to the synthesis of a variety of chiral tetracyclic indenopyrazolopyrazolone frameworks. The study revealed the stepwise annulation process catalyzed by Rh(III) and the coordination mode of dual directing groups in tuning the selectivity.

CHINESE CHEMICAL LETTERS (2022)

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Article Chemistry, Organic

Asymmetric Synthesis of Chiral Aza-macrodiolides via Iridium-Catalyzed Cascade Allylation/Macrolactonization

Qi Xiong et al.

Summary: In this study, an iridium-catalyzed cascade allylation/macrolactonization reaction was developed, which efficiently synthesizes chiral macrodiolides with excellent diastereoselectivities and enantioselectivities. This method is characterized by readily available substrates, high stereoselective control, and efficient synthetic steps.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

Pd-Catalyzed Asymmetric Allylic Substitution Cascade of Substituted 4-Hydroxy-2H-pyrones with meso-Allyl Dicarbonates

Yan Zheng et al.

Summary: An efficient Pd-catalyzed asymmetric allylic substitution cascade reaction has been developed for the synthesis of chiral compounds. The reaction achieved high yields and high enantioselectivity under temperature-controlled conditions, and can be performed on a gram scale. The resulting product is versatile and can undergo various transformations.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

Palladium-Catalyzed Asymmetric Dearomative Carbonylation of Indoles

Qiuyu Li et al.

Summary: This study presents a strategy for the asymmetric dearomatization of N-arylacyl indoles via a palladium-catalyzed tandem Heck/carbonylation reaction. The resulting indoline-3-carboxylates bear vicinal C2-aza-quaternary and C3 tertiary stereocenters with high yields and excellent enantio- and diastereoselectivities. This finding represents an important advance in the fields of asymmetric carbonylation and enantioselective dearomatization reactions.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

Pd-Catalyzed Asymmetric Three-Component Allenol Carbopalladation and Allylic Cycloaddition Cascade: A Route to Functionalized Tetrahydrofurans

Hongfang Li et al.

Summary: The first Pd-catalyzed asymmetric three-component reaction of 2,3-allenol, aryl iodides, and 2-arylmethylenemolononitriles has been developed, allowing rapid access to substituted tetrahydrofurans with diverse functional groups in good yields and high selectivities. The concise total synthesis of a lignan, (-)-2-episesaminone, has been achieved using a functionalized tetrahydrofuran obtained from this reaction.

ORGANIC LETTERS (2022)

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Article Chemistry, Physical

Enantioselective Au(I)-Catalyzed Multicomponent Annulations via Tethered Counterion-Directed Catalysis

Zhenhao Zhang et al.

Summary: This study presents a new gold(I) catalyst for highly enantioselective multicomponent reactions between aldehydes, hydroxylamines, and cyclic yne-enones. The method shows broad applicability and achieves high yields, total diastereoselectivity, and high enantiomeric excess.

ACS CATALYSIS (2022)

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Article Chemistry, Applied

Silver-Catalyzed Asymmetric Aldol Reaction of Isocyanoacetic Acid Derivatives Enabled by Cooperative Participation of Classical and Nonclassical Hydrogen Bonds

Satoshi Sakai et al.

Summary: The silver-catalyzed asymmetric aldol reaction of isocyanoacetic acid derivatives with aldehydes has been developed using a chiral prolinol-phosphine ligand as a hydrogen-bond-donating P,N,O ligand. DFT calculations revealed a stepwise reaction mechanism, involving C-C bond formation and subsequent enantioselectivity-determining ring formation. The prolinol moiety of the ligand activates the aldehyde through a two-point hydrogen bond, facilitating the stereocontrolled cyclization. Additional nonclassical hydrogen bonds and London dispersion interactions may also contribute to stereocontrol.

ADVANCED SYNTHESIS & CATALYSIS (2022)

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Article Chemistry, Multidisciplinary

Asymmetric Gold(I)-Catalyzed Tandem Hydroarylation-Nazarov Cyclization: Enantioselective Access to Cyclopentenones

Marta Solas et al.

Summary: This study describes the asymmetric synthesis of cyclopentachromenones from gold-catalyzed reaction of readily available skipped alkenynones. The cascade reaction involves an initial anti-Michael hydroarylation and a subsequent Nazarov cyclization. Excellent enantiomeric ratios and chemical yields are achieved under mild reaction conditions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Review Chemistry, Inorganic & Nuclear

Recent developments in enantioselective titanium-catalyzed transformations

Helene Pellissier

Summary: This review presents the recent advancements in the field of enantioselective titanium-catalyzed transformations since the beginning of 2015, demonstrating the effectiveness of chiral green titanium catalysts in promoting various types of reactions. A previous review in a book published in 2016 covered the literature up to the end of 2014. Over the past seven years, a range of highly efficient reactions have been developed.

COORDINATION CHEMISTRY REVIEWS (2022)

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Article Chemistry, Multidisciplinary

Enantioselective Pd-catalyzed dearomative reductive Heck and domino Heck-Suzuki reactions of 2-CF3-indoles

Ren-Xiao Liang et al.

Summary: Highly enantioselective palladium-catalyzed dearomative reductive Heck reaction and domino Heck-Suzuki reaction of 2-CF3-indoles have been developed. A variety of indolines bearing different stereocenters can be obtained using different reaction systems.

CHEMICAL COMMUNICATIONS (2022)

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Review Chemistry, Multidisciplinary

Recent Advances of Catalytic Enantioselective Heck Reactions and Reductive-Heck Reactions

Jia-Qi Xie et al.

Summary: This review focuses on recent development of catalytic asymmetric Heck reaction and reductive Heck reaction, covering intermolecular and intramolecular versions since 2011. The article is organized in terms of the catalysts and olefin substrates, providing a clear structure for readers.

CHINESE JOURNAL OF CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Stereoselective 1,2-Dicarbofunctionalization of Trisubstituted Alkenes by Palladium-Catalyzed Heck/Suzuki or Heck/Sonogashira Domino Sequence

Jia-Wen Zhu et al.

Summary: This study reports the highly enantioselective and diastereoselective synthesis of a range of 3,3'-spirooxindoles through a palladium-catalyzed domino sequence, showcasing high enantioselectivities and excellent diastereoselectivities.

CCS CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Catalytic Enantioselective Aminopalladation-Heck Cascade

Yu-Ping He et al.

Summary: Domino processes initiated by intramolecular nucleopalladation of alkynes have been developed as powerful synthetic tools for functionalized heterocycle synthesis, but catalytic enantioselective versions of these reactions are scarce. By reacting 2-alkynylanilines with prochiral cyclopentenes in the presence of specific catalysts and oxidants, structurally diverse indole-cyclopentene conjugates bearing two stereocenters can be obtained in a highly diastereo- and enantio-selective manner, with one product convertible to heavily functionalized tetracyclic indolinone derivative.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Organic

Enantioselective Synthesis of Indole-Fused Bicyclo[3.2.1]octanes via Palladium(II)-Catalyzed Cascade Reaction

Gang Wang et al.

Summary: This paper presents an enantioselective construction method for indole-fused bicyclo[3.2.1]octanes, utilizing a Heck-type reaction triggered by aminopalladition to achieve construction of an all-carbon quaternary bridgehead stereocenter, with mild conditions and good tolerance for various functional groups. The method can be scaled up to demonstrate practicality.

ORGANIC LETTERS (2021)

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Review Chemistry, Organic

Enantioselective Indium-Catalyzed Transformations

Helene Pellissier

Summary: Enantioselective indium-catalyzed transformations have become a promising research field, offering the potential to replace toxic metals with greener processes in the near future.

SYNTHESIS-STUTTGART (2021)

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Article Chemistry, Organic

Palladium-Catalyzed Asymmetric Intramolecular Dearomative Heck Annulation of Aryl Halides to Furnish Indolines

Yuanfeng Li et al.

Summary: A novel Pd-catalyzed asymmetric intra-molecular cascade cyclization has been developed for the synthesis of indoline derivatives through a dearomative Heck reaction, showing excellent yields and chiral selectivities.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Asymmetric Domino Heck/Dearomatization Reaction of β-Naphthols to Construct Indole-Terpenoid Frameworks

Dong-Chao Wang et al.

Summary: The palladium-catalyzed enantioselective Heck cyclization/dearomatization cascade via capturing the cyclized Heck pi-allylpalladium intermediate by beta-naphthols provides a new strategy for constructing chiral indole-terpenoid frameworks. This method yields indole-functionalized beta-naphthalenone compounds with all-carbon-substituted quaternary chiral centers in excellent yields (up to 92%) and enantioselectivities (up to 94% ee), with demonstrated utility in gram-scale syntheses and diverse transformations of the dearomatized products.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Enantioselective Synthesis of α-All-Carbon Quaternary Center-Containing Carbazolones via Amino-palladation/Desymmetrizing Nitrile Addition Cascade

Xu-Dong Hu et al.

Summary: This research presents an efficient enantioselective Pd(II)-catalyzed cascade reaction for the transformation of alkyne-tethered malononitriles into alpha-quaternary carbazolones with high enantioselectivities. The utility of this method is demonstrated by the synthesis of diverse heterocycles and a nitrile-containing leucomidine A analog from the obtained products.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Organic

Asymmetric Synthesis of γ-Lactams Containing α,β-Contiguous Stereocenters via Pd(II)-Catalyzed Cascade Methylene C(sp3)-H Alkenylation/Aza-Wacker Cyclization

Le-Song Wu et al.

Summary: The paper describes an asymmetric C-H activation strategy for accessing alpha,beta-stereospecific gamma-lactams in good yields with high enantio- and diastereoselectivities, serving as an effective supplement to existing strategies.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Iridium-Catalyzed Asymmetric Cascade Allylation/Pictet-Spengler Cyclization Reaction for the Enantioselective Synthesis of 1,3,4-Trisubstituted Tetrahydroisoquinolines

Wu-Lin Yang et al.

Summary: An iridium-catalyzed trifluoroacetic acid-promoted asymmetric cascade allylation/Pictet-Spengler cyclization reaction of azomethine ylides with aromatic allylic alcohols is reported, providing a facile and scalable method for the construction of 1,3,4-trisubstituted tetrahydroisoquinolines containing two stereogenic centers in good yields with generally excellent diastereo- and enantioselectivities. Additionally, a series of aromatic heterocyclefused piperidines were also obtained with excellent enantiocontrol by this methodology.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Pd-Catalyzed Enantioselective Dicarbofunctionalization of Alkene to Access Disubstituted Dihydroisoquinolinone

Qiaoyu Chen et al.

Summary: A Pd/Xu-Phos-catalyzed asymmetric Heck/Suzuki domino reaction has been developed, demonstrating high functional group tolerance and the ability to couple with various aryl/alkenyl borates. A series of chiral disubstituted dihydroisoquinolinones were obtained in good yields and excellent enantioselectivities.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Palladium-Catalyzed Enantioselective 7-exo-Trig Carbopalladation/Carbonylation: Cascade Reactions To Achieve Atropisomeric Dibenzo[b,d]azepin-6-ones

Huaanzi Hu et al.

Summary: Enantioselective 7-exo-trig cyclocarbopalladation-initiated carbonylation cascade reactions have been successfully achieved, yielding seven-membered dibenzo[b,d]azepin-6-ones with a thermodynamically controlled stereogenic axis and excellent diastereo- and enantioselectivities. The calculated energy difference between diastereoisomers is approximately 2.8 kcal/mol, explaining the observed high diastereoselectivity.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Stereoselective construction of fused cyclopropane from ynamide and its application to synthesis of small drug candidate molecules

Tsubasa Ito et al.

Summary: An asymmetric intramolecular cyclopropanation reaction under silver catalysis has been developed, producing enantioenriched gamma-lactam fused cyclopropane commonly found in bioactive molecules and pharmaceuticals. The fused cyclopropane was efficiently converted into drug candidate molecules in short steps, highlighting the utility of this method. Computational investigations based on density functional theory clarified the chemoselectivity between the desired cyclopropanation and overoxidation process observed experimentally.

TETRAHEDRON LETTERS (2021)

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Article Chemistry, Multidisciplinary

Enantioselective Synthesis of Spiro-oxiranes: An Asymmetric Addition/Aldol/Spirocyclization Domino Cascade

Ken-Loon Choo et al.

Summary: Enantioenriched spiro-oxiranes with three contiguous stereocenters were synthesized using a rhodium-catalyzed cascade reaction, enabling the formation of a spirocyclic framework in a single step. Both sp(2)- and sp-hybridized carbon nucleophiles were found to be efficient initiators, yielding products with different functional groups. Derivatization studies demonstrated the synthetic versatility of the products' epoxide and alkyne moieties. DFT calculations were employed to explain spectroscopic discrepancies between solution- and solid-state structures of the products.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Silver-Catalyzed Asymmetric Dearomatization of Electron-Deficient Heteroarenes via Interrupted Barton-Zard Reaction

Qian Wan et al.

Summary: In this study, a catalytic asymmetric dearomatization reaction of electron-deficient heteroarenes with alpha-substituted isocyanoacetates was reported, leading to a range of optically active pyrrolo[3,4-b]indole derivatives. The reaction yielded good results with high stereoselectivities, using a catalytic system consisting of a cinchona-derived amino-phosphine and silver oxide. This method features wide substrate scope, mild conditions, and provides a new strategy for developing asymmetric dearomatization reactions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Sequential Pd0- and PdII-Catalyzed Cyclizations: Enantioselective Heck and Nucleopalladation Reactions

Andrew Whyte et al.

Summary: An enantioselective consecutive cyclization/coupling process catalyzed by palladium was reported in this study. The stereoinduction was achieved through an enantioselective carbopalladation, leading to the generation of an intermediate that promotes a nucleopalladation step. This dual cyclization sequence was compatible with various nucleophiles and aryl iodides, producing numerous bisheterocycles in good yields and high regio- and enantioselectivities.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Asymmetric Domino Heck/Carbocyclization/Suzuki Reaction: A Dearomatization of Nonactivated Naphthalenes

Ming Chen et al.

Summary: In this study, a novel palladium-catalyzed asymmetric domino Heck/carbocyclization/Suzuki reaction of N-(2-bromoaryl)-2-naphthylacrylamides was reported. The reaction involved a unique enantioselective dearomative 1,2-insertion of the naphthalene group, providing a novel dearomatization strategy for nonactivated naphthalenes. A new phosphoramidite ligand L12 was developed, displaying excellent reactivity and enantioselectivity in the reaction, allowing for the straightforward synthesis of spirooxindoles bearing three stereogenic centers in high yields under mild conditions.

CCS CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Palladium/Xu-Phos Catalyzed Enantioselective Tandem Heck/Cacchi Reaction of Unactivated Alkenes

Yi Wu et al.

Summary: A highly enantioselective palladium-catalyzed intermolecular tandem Heck/Cacchi reaction was developed for the synthesis of a broad range of enantioenriched compounds bearing all-carbon quaternary stereocenters of interest in pharmaceutical research. This method features inherent atom- and step-economy, high functional group tolerance, mild conditions, broad structural diversity, and excellent enantioselectivities.

CHINESE JOURNAL OF CHEMISTRY (2021)

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Article Chemistry, Organic

Enantioselective Synthesis of Fused Isocoumarins via Palladium-Catalyzed Annulation of Alkyne-Tethered Malononitriles

Hui Zhang et al.

Summary: This enantioselective palladium-catalyzed annulation reaction allows for the synthesis of 3,4-ring-fused isocoumarins by simultaneously constructing two rings and a quaternary stereocenter in one operation.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Construction of Atropisomeric 3-Arylindoles via Enantioselective Cacchi Reaction

Xiaojiao Li et al.

Summary: The de novo construction of axially chiral 3-arylindoles bearing a C(3)-C(aryl) chiral axis has been successfully achieved through a Pd-catalyzed enantioselective Cacchi reaction between aryl bromides and o-alkynylanilines. The reaction proceeds under mild conditions with high yields and excellent enantioselectivities.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Catalytic Asymmetric Tandem Reaction of o-Alkynylbenzaldehydes, Amines, and Diazo Compounds

Wei Wu et al.

Summary: An efficient asymmetric tandem reaction catalyzed by chiral silver imidodiphosphate has been developed for the synthesis of chiral 1,2-dihydroisoquinoline analogues with a tertiary stereocenter at the C1 position. The products can be further elaborated into beta-aminophosphonates or PARP1-inhibitor analogues with high yields and ee values.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Enantioselective palladium-catalyzed C(sp2)-C(sp2) σ bond activation of cyclopropenones by merging desymmetrization and (3+2) spiroannulation with cyclic 1,3-diketones

Han-Qi Zhou et al.

Summary: Catalytic asymmetric variants for functional group transformations based on carbon-carbon bond activation are still challenging to achieve. Here, a palladium-catalyzed (3 + 2) spiro-annulation process is presented, merging C(sp(2))-C(sp(2)) sigma bond activation and click desymmetrization to form synthetically versatile oxaspiro products. The operationally straightforward and enantioselective process uses a bulky P-ligand to control enantioselective spiro-annulation, converting cyclopropenones and cyclic 1,3-diketones into chiral oxaspiro cyclopentenone-lactone scaffolds.

CHEMICAL SCIENCE (2021)

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Article Chemistry, Multidisciplinary

Palladium-catalysed imidoylative spirocyclization of 3-(2-isocyanoethyl)indoles

Shi Tang et al.

Summary: A palladium-catalysed construction of spiroindolines has been developed through dearomative spirocyclization of 3-(2-isocyanoethyl)indoles, yielding a variety of spiroindolines and bisheterocyclic compounds with high yields and enantioselectivity.

CHEMICAL COMMUNICATIONS (2021)

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Article Chemistry, Multidisciplinary

Enantioselective synthesis of polycyclic pyrrole derivatives by iridium-catalyzed asymmetric allylic dearomatization and ring-expansive migration reactions

Lin Huang et al.

Summary: This study presents a novel N-alkylation of pyrroles through an Ir-catalyzed asymmetric allylic dearomatization-induced selective ring-expansive migration, providing a series of tetrahydropyrrolo[1,2-c]pyrimidine derivatives with good yields and excellent enantioselectivity. The proposed reaction mechanism is supported by DFT calculations and the characterization of the key intermediate.

CHEMICAL COMMUNICATIONS (2021)

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Article Chemistry, Organic

Constructing chiral aza-quaternary carbon centers by enantioselective carbonylative Heck reaction of o-iodoanilines with allenes

Zhengshuai Xu et al.

Summary: This research achieved the construction of chiral aza-quaternary carbon centers via C-N bond formation, providing chiral dihydroquinolinone derivatives with moderate to high yield and improved enantiomeric ratio. The use of a syringe pump to add o-iodoaniline was crucial in reducing side reactions and improving chemoselectivity. By utilizing the chirality induction of an assembled aza-quaternary stereogenic center, molecules with vicinal chiral quaternary carbon centers or multiple chiral centers can be rapidly prepared.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Organic

A rhodium-catalysed conjugate addition/cyclization cascade for the asymmetric synthesis of 2-amino-4H-chromenes

Zhiqian Chang et al.

Summary: The enantioselective synthesis of 2-amino-4H-chromenes via cascade rhodium-catalysed conjugate addition/hetero Thorpe-Ziegler reaction achieved moderate to good yields (up to 98%) and high enantioselectivities (up to 92% ee) using a chiral diene-coordinated rhodium complex as the catalyst. This protocol addresses the methodological deficiency in the asymmetric synthesis of 4-aryl 2-amino-4H-chromenes.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Review Chemistry, Multidisciplinary

Asymmetric desymmetrization of alkene-, alkyne- and allene-tethered cyclohexadienones using transition metal catalysis

Tao Shu et al.

Summary: By utilizing transition metals and chiral ligands in catalytic asymmetric domino reactions, desymmetrization of alkene-, alkyne- and allene-tethered cyclohexadienones can be achieved, allowing for rapid construction of complex molecular frameworks and control of multiple stereogenic centers.

CHEMICAL SOCIETY REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Enantioselective Difunctionalization of Alkenes by a Palladium-Catalyzed Heck/Sonogashira Sequence

Lujia Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Asymmetric Wacker-Type Oxyallenylation and Azaallenylation of Cyclic Alkenes

Shenghan Teng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Enantioselective Cacchi Reaction: Asymmetric Synthesis of Axially Chiral 2,3-Disubstituted Indoles

Yu-Ping He et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Catalytic Domino Annulations through η3-Allylpalladium Chemistry: A Never-Ending Story

Yang Liu et al.

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY (2020)

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Tethered Counterion-Directed Catalysis: Merging the Chiral Ion-Pairing and Bifunctional Ligand Strategies in Enantioselective Gold(I) Catalysis

Zhenhao Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Organic

Highly Enantioselective Ruthenium-Catalyzed Cascade Double Reduction Strategy: Construction of Structurally Diverse Julolidines and Their Analogues

Li-Ren Wang et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Multidisciplinary

Pd(II)-Catalyzed Tandem Enantioselective Methylene C(sp3)-H Alkenylation-Aza-Wacker Cyclization to Access β-Stereogenic γ-Lactams

Yi Ding et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Enantioselective Heck Carbonylation with a Monodentate Phosphoramidite Ligand: Asymmetric Synthesis of (+)-Physostigmine, (+)-Physovenine, and (+)-Folicanthine

Ming Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Physical

Endo-Selective Construction of Spiro-[butyrolactone-pyrrolidine] via Ag(I)/CAAA-Amidphos-Catalyzed 1,3-Dipolar Cycloaddition between Azomethine Ylides and α-Methylene-γ-Butyrolactone

Qinglin Hou et al.

CATALYSTS (2020)

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Article Multidisciplinary Sciences

Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes

Zhenbo Yuan et al.

NATURE COMMUNICATIONS (2020)

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Direct Synthesis of Chiral NH Lactams via Ru-Catalyzed Asymmetric Reductive Amination/Cyclization Cascade of Keto Acids/Esters

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Highly Enantioselective Rhodium-Catalyzed Cross-Addition of Silylacetylenes to Cyclohexadienone-Tethered Internal Alkynes

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Switching Diastereoselectivity in Catalytic Enantioselective (3+2) Cycloadditions of Azomethine Ylides Promoted by Metal Salts and Privileged Segphos-Derived Ligands

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Palladium-Catalyzed Asymmetric Tandem [3+2] Cycloaddition/Allylation Reaction of Methylene-Trimethylenemethane: Access to Chiral Tricyclic Dinitrogen-Fused Heterocycles

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Asymmetric Palladium-Catalyzed C-H Functionalization Cascade for Synthesis of Chiral 3,4-Dihydroisoquinolones

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Rhodium(III)-Catalyzed Asymmetric Borylative Cyclization of Cyclohexadienone-Containing 1,6-Dienes: An Experimental and DFT Study

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Palladium(II)-Catalyzed Reductive Cyclization of N-Tosyl-Tethered 1,7-Enynes: Enantioselective Synthesis of 1,2,3,4-Tetrahydroquinolines

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Enantioenriched 1-Tetralones via Rhodium-Catalyzed Arylative Cascade Desymmetrization/Acylation of Alkynylmalonates

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Enantioselective Dicarbofunctionalization of Unactivated Alkenes by Palladium-Catalyzed Tandem Heck/Suzuki Coupling Reaction

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Highly Enantioselective Iridium-Catalyzed Cascade Double Allylation Strategy: Synthesis of Pyrrolidinoindolines with an All-Carbon Quaternary Stereocenter

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Enantioselective Ruthenium(II)-Catalyzed Access to Benzonorcaradienes by Coupling of Oxabenzonorbornadienes and Alkynes

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Recent Developments in Enantioselective Metal-Catalyzed Domino Reactions

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Catalytic Atropenantioselective Heteroannulation between Isocyanoacetates and Alkynyl Ketones: Synthesis of Enantioenriched Axially Chiral 3-Arylpyrroles

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Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues via Ruthenium-Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination

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Enantioselective Synthesis of 5-Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis

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Synthesis of Chiral 3-Substituted 3-Amino-2-oxindoles through Enantioselective Catalytic Domino and Tandem Reactions

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Enantioselective Synthesis of Chiral Medium-Sized Cyclic Compounds via Tandem Cycloaddition/Cope Rearrangement Strategy

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Enantioselective synthesis of quaternary 3,4-dihydroisoquinolinones via Heck carbonylation reactions: development and application to the synthesis of Minalrestat analogues

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A new trifluoromethylated sulfonamide phosphine ligand for Ag(I)-catalyzed enantioselective [3+2] cycloaddition of azomethine ylides

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Catalytic asymmetric synthesis of 2,5-dihydrofurans using synergistic bifunctional Ag catalysis

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Access to chiral tetrahydrofluorenes through a palladium-catalyzed enantioselective tandem intramolecular Heck/Tsuji-Trost reaction

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Catalytic asymmetric cycloaddition of unsymmetrical EWG-activated alkenes to fully substituted pyrrolidines bearing three different carbonyl groups

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Hydroalkynylative cyclization of 1,6-enynes with terminal alkynes

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Increasing Catalyst Efficiency in C-H Activation Catalysis

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Transition-Metal-Catalyzed Selective Functionalization of C(sp(3))-H Bonds in Natural Products

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Review Chemistry, Organic

Synthesis of chiral 3-substituted 3-amino-2-oxindoles through enantioselective catalytic nucleophilic additions to isatin imines

Helene Pellissier

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Review Chemistry, Multidisciplinary

Pd Metal Catalysts for Cross-Couplings and Related Reactions in the 21st Century: A Critical Review

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Review Chemistry, Inorganic & Nuclear

Recent developments in enantioselective cobalt-catalyzed transformations

Helene Pellissier

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Review Chemistry, Organic

Recent Developments in Enantioselective Organocatalytic Michael Reactions in Aqueous Media

Helene Pellissier

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C-O Bonds from Pd-Catalyzed C(sp3)-H Reactions Mediated by Heteroatomic Groups

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Recent Progress in Palladium-Catalyzed Cascade Cyclizations for Natural Product Synthesis

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Recent Advances in Palladium-Catalyzed Cross-Coupling Reactions at ppm to ppb Molar Catalyst Loadings

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CHEMICAL REVIEWS (2017)

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Metal-catalyzed C-H activation/functionalization: The fundamentals

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Enantioselective magnesium-catalyzed transformations

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ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

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Review Chemistry, Organic

Cyclocarbopalladation as a Key Step in Cascade Reactions: Recent Developments

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Recent Developments in Palladium-Catalyzed Oxidative Cascade Carbocyclization

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Review Chemistry, Organic

Recent Developments in Pd0-Catalyzed Alkene-Carboheterofunctionalization Reactions

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Transition-Metal-Catalyzed C-H Alkylation Using Alkenes

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Review Chemistry, Multidisciplinary

Catalytic Enantioselective Transformations Involving C-H Bond Cleavage by Transition-Metal Complexes

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Recent Catalytic Asymmetric Syntheses of 3,3-Disubstituted Indolin-2-ones and 2,2-Disubstituted Indolin-3-ones

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Review Chemistry, Medicinal

Palladium(0)-Catalyzed Benzylic C(sp3)-H Functionalization for the Concise Synthesis of Heterocycles and Its Applications

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σ-Alkyl-PdII Species for Remote C-H Functionalization

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CHEMCATCHEM (2017)

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Review Chemistry, Applied

Recent Developments in Enantioselective Metal-Catalyzed Domino Reactions

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Review Chemistry, Multidisciplinary

Enantioselective Silver-Catalyzed Transformations

Helene Pellissier

CHEMICAL REVIEWS (2016)

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Review Chemistry, Organic

Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups

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Review Chemistry, Organic

Silver and gold-catalyzed multicomponent reactions

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Review Chemistry, Multidisciplinary

Enantioselective Cobalt-Catalyzed Transformations

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CHEMICAL REVIEWS (2014)

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Review Chemistry, Multidisciplinary

Stereocontrolled Domino Reactions

Helene Pellissier

CHEMICAL REVIEWS (2013)

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Review Chemistry, Multidisciplinary

Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations

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CHEMICAL REVIEWS (2013)

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Review Chemistry, Applied

Recent Developments in Asymmetric Organocatalytic Domino Reactions

Helene Pellissier

ADVANCED SYNTHESIS & CATALYSIS (2012)

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Review Chemistry, Applied

Recent Developments in Enantioselective Metal-Catalyzed Domino Reactions

Herve Clavier et al.

ADVANCED SYNTHESIS & CATALYSIS (2012)

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Review Chemistry, Multidisciplinary

Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize

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Enantioselective Zinc-Catalyzed Hydrosilylation of Ketones using Pybox or Pybim Ligands

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Review Chemistry, Organic

Heterocycle Formation via Palladium-Catalyzed C-H Functionalization

Tian-Sheng Mei et al.

SYNTHESIS-STUTTGART (2012)

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Review Chemistry, Organic

Recent Developments in Palladium-Catalyzed Formation of Five-and Six-Membered Fused Heterocycles

K. C. Majumdar et al.

SYNTHESIS-STUTTGART (2012)

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Review Chemistry, Applied

Recent Advances in Palladium-Catalyzed Cascade Cyclizations

Tjostil Vlaar et al.

ADVANCED SYNTHESIS & CATALYSIS (2011)

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Review Chemistry, Multidisciplinary

Update 1 of: C-2-Symmetric Chiral Bis(oxazoline) Ligands in Asymmetric Catalysis

Giovanni Desimoni et al.

CHEMICAL REVIEWS (2011)

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Review Chemistry, Multidisciplinary

The asymmetric Heck and related reactions

Dennis Mc Cartney et al.

CHEMICAL SOCIETY REVIEWS (2011)

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Review Chemistry, Multidisciplinary

Natural Product Synthesis Using Multicomponent Reaction Strategies

Barry B. Toure et al.

CHEMICAL REVIEWS (2009)

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Review Chemistry, Multidisciplinary

Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and Their Salts: Practical Alternatives to Boron- and Tin-Based Methods

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ACCOUNTS OF CHEMICAL RESEARCH (2008)

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Review Chemistry, Multidisciplinary

Biaryl phosphane ligands in palladium-catalyzed amination

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

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Review Chemistry, Multidisciplinary

Silver-mediated synthesis of heterocycles

Miriam Alvarez-Corral et al.

CHEMICAL REVIEWS (2008)

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Review Chemistry, Multidisciplinary

Asymmetric silver-catalyzed reactions

Marina Naodovic et al.

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Review Multidisciplinary Sciences

Carbon-heteroatom bond formation catalysed by organometallic complexes

John F. Hartwig

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C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents

Egle M. Beccalli et al.

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Review Chemistry, Inorganic & Nuclear

Organocatalytic enantioselective multicomponent reactions (OEMCRs)

Gabriela Guillena et al.

TETRAHEDRON-ASYMMETRY (2007)

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Review Chemistry, Multidisciplinary

Asymmetric organocatalytic domino reactions

Dieter Enders et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

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Review Chemistry, Organic

Asymmetric domino reactions. Part B: Reactions based on the use of chiral catalysts and biocatalysts

H Pelissier

TETRAHEDRON (2006)

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Review Chemistry, Organic

Asymmetric domino reactions. Part A: Reactions based on the use of chiral auxiliaries

H Pellissier

TETRAHEDRON (2006)

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In the arena of enantioselective synthesis, titanium complexes wear the laurel wreath

Diego J. Ramon et al.

CHEMICAL REVIEWS (2006)

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Review Chemistry, Multidisciplinary

Asymmetric multicomponent reactions (AMCRs): The new frontier

DJ Ramon et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

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Review Chemistry, Multidisciplinary

Enantioselective palladium-catalyzed transformations

LF Tietze et al.

CHEMICAL REVIEWS (2004)

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Review Chemistry, Multidisciplinary

In the golden age of organocatalysis

PI Dalko et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2004)

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Review Chemistry, Multidisciplinary

The asymmetric intramolecular Heck reaction in natural product total synthesis

AB Dounay et al.

CHEMICAL REVIEWS (2003)

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Article Chemistry, Inorganic & Nuclear

How I came across the silicon-based cross-coupling reaction

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Article Chemistry, Inorganic & Nuclear

New cascade and multiple cross-coupling reactions for the efficient construction of complex molecules

A de Meijere et al.

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Review Chemistry, Organic

Palladium in organic synthesis: Fundamental transformations and domino processes

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TETRAHEDRON (2000)

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Review Chemistry, Multidisciplinary

The heck reaction as a sharpening stone of palladium catalysis

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CHEMICAL REVIEWS (2000)

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