4.5 Review

Recent Advances in Base-assisted Michael Addition Reactions

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Convenient synthesis of hexasubstituted benzene derivatives via DABCO promoted domino reaction of arylidene malononitrile and dialkyl but-2-ynedioate

Hui Zheng et al.

Summary: In summary, a convenient synthetic protocol for hexasubstituted benzene derivatives was successfully developed through DABCO-promoted domino reaction. The reaction mechanism involves sequential nucleophilic addition, Michael addition, annulation, and aromatization processes.

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Controllable Lewis Base Catalyzed Michael Addition of α-Aminonitriles to Activated Alkenes: Facile Synthesis of Functionalized γ-Amino Acid Esters and γ-Lactams

Ze-Ying He et al.

Summary: A novel protocol for the synthesis of functionalized gamma-amino acid esters and gamma-lactams through a controllable Lewis base catalyzed Michael addition of alpha-aminonitriles to simple activated alkenes has been developed, demonstrating the scope, versatility, and efficiency of the process.

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Synthesis of trifluoromethyl substituted nucleophilic glycine equivalents and the investigation of their potential for the preparation of α-amino acids

Mackenzie Bergagnini-Kolev et al.

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A green and novel method for synthesis of β-sulfonyl esters under solvent-free conditions

Gholamhassan Imanzadeh et al.

Summary: This method for the synthesis of beta-sulfonyl esters from sulfonyl hydrazides and acrylic esters, promoted by DABCO, is a manipulative, simple, and efficient green approach conducted through sulfa-Michael addition reaction at 75 degrees C within 2-3 hours. The effects of different bases, molar ratio of DABCO, temperature, and time parameters on yield of reaction were investigated.

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Recoverable Phospha-Michael Additions Catalyzed by a 4-N,N-Dimethylaminopyridinium Saccharinate Salt or a Fluorous Long-Chained Pyridine: Two Types of Reusable Base Catalysts

Eskedar Tessema et al.

Summary: Phospha-Michael addition is a versatile tool for the formation of P-C bonds, offering the possibility to access diverse functionalized products. The use of DMAP∙Hsac and fluorous long-chained pyridine as catalysts efficiently catalyzes the addition reactions, with high reactivity and good catalytic recovery and reusability. The easy separation of catalysts from products demonstrates the outstanding efficacy of the systems.

MOLECULES (2021)

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DMAP-Catalyzed Reaction of Diethyl 1,3-Acetonedicarboxylate with 2-Hydroxybenzylideneindenediones: Facile Synthesis of Fluorenone-Fused Coumarins

Mohanad Shkoor et al.

Summary: The base-catalyzed reaction of two compounds provides a convenient and efficient method for the synthesis of natural product inspired fluorenone-fused coumarins in good to very good yields. This protocol resembles a combination of multiple reactions in a single step.

SYNLETT (2021)

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Organo-catalyzed Michael addition of 2-fluoro-2-arylacetonitriles

De-Yin Chen et al.

Summary: An efficient synthesis method for 2-arylacetonitriles containing a fluorinated stereogenic center has been developed through organo-catalyzed Michael addition reaction. The use of a cheap organocatalyst (DBU) allows for a broad substrate scope, including alpha, beta-unsaturated ketones, esters, nitriles, and sulfones. Importantly, water has been found to be a suitable solvent for this reaction.

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One-Pot Synthesis of 1,5-Diketones under a Transition-Metal-Free Condition: Application in the Synthesis of 2,4,6-Triaryl Pyridine Derivatives

Kesatebrhan Haile Asressu et al.

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Asymmetric hetero-Michael addition to α,β-unsaturated carboxylic acids using thioureaeboronic acid hybrid catalysts

Noboru Hayama et al.

Summary: This review summarizes the first catalytic asymmetric Michael addition of heteroatomic nucleophiles to alpha,beta-unsaturated carboxylic acids. Hybrid catalysts are designed to activate the unsaturated carboxylic acids, leading to synthetic applications to biologically active compounds. The mechanistic consideration of multicomponent borate complexes is also discussed in this work.

TETRAHEDRON (2021)

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Cesium Carbonate Catalyzed Oxa-Michael Addition of Oximes to Acrylonitrile

Jessica Stahl et al.

Summary: Researchers reported the O-alkylation of oximes with Michael acceptors using Cs2CO3 as the catalyst, achieving stereospecific transformation with retention of oxime configuration. Irradiation with visible light in the presence of diphenyl anthracene and cerium complexes affected the E to Z configuration ratio of the oxime ether products, but complete stereocontrol was not achieved. The operationally simple protocol allows the synthesis of various O-alkylated oxime products useful as precursors for further chemical transformations.

CHEMISTRYSELECT (2021)

Article Chemistry, Applied

Potassium Base-Catalyzed Michael Additions of Allylic Alcohols to α,β-Unsaturated Amides: Scope and Mechanistic Insights

Masahiro Sai et al.

Summary: In this study, the first KHMDS-catalyzed Michael additions of allylic alcohols to alpha,beta-unsaturated amides were reported. The reaction proceeds smoothly with only 5 mol% of KHMDS to afford a variety of 1,5-ketoamides in high yields. Mechanistic investigations revealed that the in-situ generation of the enolate from the allylic alcohol through a tunneling-assisted 1,2-hydride shift is crucial for the success of this transformation.

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Ashes from organic waste as reagents in synthetic chemistry: a review

Katta Venkateswarlu

Summary: The article reviews the recycling of biomass ashes into reagents for chemical synthesis and biodiesel production, including various chemical reactions and the synthesis of compounds.

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Intermolecular domino Michael/aldol reactions of α,β-unsaturated esters, aromatic aldehydes, and various nucleophiles promoted with a catalytic amount of a guanidine base in DMSO

Shunya Morita et al.

Summary: In DMSO, a catalytic amount of Barton's base (BTMG) effectively catalyzed intermolecular three-component reactions, forming new three-component addition products with the reaction of α, β-unsaturated esters, aldehydes, and carbon-, sulfur-, or nitrogen-pronucleophiles. The mechanism involves the formation of anionic nucleophiles from pronucleophiles catalyzed by BTMG, followed by intermolecular aldol reactions of transient ester enolates.

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Highly diastereoselective four-component synthesis of polysubstituted 2-piperidinones with three and four stereogenic centers

Anatoly N. Vereshchagin et al.

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KOtBu-Catalyzed Michael Addition Reactions Under Mild and Solvent-Free Conditions

Subramanian Thiyagarajan et al.

CHEMISTRY-AN ASIAN JOURNAL (2020)

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Innovative catalysis in Michael addition reactions for C-X bond formation

Radhika S. Malkar et al.

MOLECULAR CATALYSIS (2020)

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Synthesis and Antimicrobial Activity of Some New Coumarin and Dicoumarol Derivatives

M. K. A. Regal et al.

RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY (2020)

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Recent advances in organocatalytic asymmetric oxa-Michael addition triggered cascade reactions

Yu Wang et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

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Asymmetric Synthesis of 2,3-Dihydrofurans by One-Pot Michael Addition/I-2-Mediated Cyclization

Xiao-Long Zhang et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

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A one-pot access to pyridine/benzo fused cyclododecanes via multi-component tandem reactions

Sundaravel Vivek Kumar et al.

TETRAHEDRON (2018)

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Thia-Michael Addition: An Emerging Strategy in Organic Synthesis

Preeti Wadhwa et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2018)

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Design, synthesis and in vitro -glucosidase inhibition of novel coumarin-pyridines as potent antidiabetic agents

Mehdi Adib et al.

NEW JOURNAL OF CHEMISTRY (2018)

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Synthesis of indole-cycloalkyl[b]pyridine hybrids via a four-component six-step tandem process

Muthumani Muthu et al.

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Polymer-Shell-Encapsulated Magnetite Nanoparticles Bearing Hexamethylenetetramine for Catalysing Aza-Michael Addition Reactions

Prakash B. Rathod et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

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Synthesis and Recovery of Pyridine- and Piperidine-based Camphorsulfonamide Organocatalysts Used for Michael Addition Reaction

Peter Kisszekelyi et al.

PERIODICA POLYTECHNICA-CHEMICAL ENGINEERING (2018)

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Metal-Catalyzed Asymmetric Michael Addition in Natural Product Synthesis

Chunngai Hui et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

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Recent topics on catalytic asymmetric 1,4-addition

Masahiko Hayashi et al.

TETRAHEDRON LETTERS (2017)

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Conjugated nitrosoalkenes as Michael acceptors in carbon-carbon bond forming reactions: a review and perspective

Yaroslav D. Boyko et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2017)

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Microwave Irradiation Accelerates 4-Dimethylaminopyridine-catalyzed Michael Addition of Phenols or Anilines

Hirokazu Iida et al.

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Microwave-assisted synthesis and antimicrobial evaluation of novel pyrazolines

Ashok Dongamanti et al.

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Higher-Order Cyclopropenimine Superbases: Direct Neutral Bronsted Base Catalyzed Michael Reactions with α-Aryl Esters

Eric D. Nacsa et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Microwave-assisted synthesis of some new coumarin-pyrazoline hybrids and their antimicrobial activity

Dongamanti Ashok et al.

JOURNAL OF THE SERBIAN CHEMICAL SOCIETY (2015)

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Asymmetric Michael addition reactions of nitroalkanes to 2-furanones catalyzed by bifunctional thiourea catalysts

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Domino four-component synthesis of novel cycloocta[b]pyridines

Seeni Maharani et al.

TETRAHEDRON LETTERS (2015)

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Enantioselective Michael Reaction of Acetals with Nitroalkenes: An Improvement of the Oseltarnivir Synthesis

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ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2015)

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Recent developments in the field of oxa-Michael reactions

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Bifunctional Organocatalysts in the Asymmetric Michael Additions of Carbonylic Compounds to Nitroalkenes

Ratnasamy Somanathan et al.

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Chiral dialkylaminopyridine catalysts in asymmetric synthesis

Ryan P. Wurz

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Widely useful DMAP-catalyzed esterification under auxiliary base- and solvent-free conditions

Akira Sakakura et al.

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