Aza‐Michael Reaction: A Decade Later – Is the Research Over?

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(26)

Published: June 14, 2023

Abstract The 1,4‐conjugated addition of nitrogen centered nucleophiles to electron‐deficient alkenes, historically called the aza‐Michael addition, is one most significant and widely used reactions in modern synthetic organic chemistry. In last decade, great progress has been made this field namely development various catalytic systems. Fundamental advances involve use transition metal catalysts, organocatalysts, enzymes, ionic liquids, Brønsted Lewis acids bases. This Review aims critically analyze results research into aliphatic aromatic amines with Michael acceptors.

Language: Английский

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Hydrazine Hydrate in Asymmetric Synthesis: A Bifunctional Squaramide Catalytic Approach toward Fused Pyrazolines

Organic Letters, Journal Year: 2023, Volume and Issue: 25(38), P. 6993 - 6998

Published: Sept. 20, 2023

A unified strategy has been developed to utilize hydrazine hydrate in asymmetric organic synthesis by overcoming the rapid background reaction with dienone. The H-bond donor ability of cinchona-alkaloid-derived squaramide catalyst unlocks this previously deemed infeasibility. dissymmetric addition symmetrical dienones tolerates various substitutions, resulting formation optically pure fused pyrazoline derivatives under mild conditions. Furthermore, scalability methodology and a successful demonstration postsynthetic transformations have accomplished.

Language: Английский

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Understanding selectivity of nucleophilic addition to β-formyl-α-haloenoates: A synthetic and theoretical investigation

Tetrahedron, Journal Year: 2024, Volume and Issue: 155, P. 133892 - 133892

Published: Feb. 22, 2024

Language: Английский

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Tandem Synthesis of Pyrrolidine and Piperidine Derivatives from Propargylic Alcohols Under Multimetallic Catalysis

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 28, 2025

Herein reported is tandem synthesis of 2‐carbonylmethyl pyrrolidine/piperidine derivatives from propargylic alcohols under multimetallic catalysis. A Meyer–Schuster rearrangement cationic Au catalysis, followed by in situ olefin cross‐metathesis with appropriately protected amino olefins delivered α,β‐unsaturated ketones, which without isolation underwent an intramolecular aza‐Michael addition to afford a variety pyrrolidine and piperidine derivatives. The scope the present reaction investigated show that common amine protecting groups, such as Ts, Ns, Cbz, Bz, are well tolerated. Addition catalytic amount bismuth(III) triflate required for promoting where N‐protected group less nucleophilic. stereochemical consequence found be dependent on group.

Language: Английский

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Advances in Transition Metal Catalysis and Organocatalysis Approaches towards Asymmetric Synthesis of β-Amino Acid Derivatives

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 16, 2024

Abstract The stereoselective synthesis of β-amino acids has attracted major attention among the synthetic community in recent years. This review provides an overview important advances chiral acid over past decade. It covers development enantioselective methods using transition-metal complexes or organocatalysts, mainly including catalytic asymmetric hydrogenation, Mannich reaction, multicomponent reactions diazo compounds, and conjugate addition. Additionally, optically active by other approaches are also summarized. 1 Introduction 2 Strategies towards Asymmetric Synthesis β-Amino Acids 2.1 Hydrogenation 2.2 Reaction 2.3 Conjugate Addition 2.4 Multicomponent Reactions 2.5 Miscellaneous 2.5.1 from Chiral Amines 2.5.2 Isoxazolidinones 2.5.3 Other Methodologies 3 Summary Outlook

Language: Английский

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New Functional Alkoxysilanes and Silatranes: Synthesis, Structure, Properties, and Possible Applications

International Journal of Molecular Sciences, Journal Year: 2023, Volume and Issue: 24(18), P. 13818 - 13818

Published: Sept. 7, 2023

The aza-Michael reaction of 3-aminopropyltriethoxysilane (1) and -silatrane (2) with acrylates affords functionalized silyl-(3–8) silatranyl-(9–14) mono- diadducts up to a 99% yield. Their structure has been proved IR NMR spectroscopies, mass spectrometry XRD analysis. hydrolytic homo-condensation triethoxysilanes 3–5 gives siloxanes 3a–5a, which form complexes Ag, Cu, Ni salts. They are also able adsorb these metals from solutions. hetero-condensation silanes 4–8 OH groups zeolite (Z), silica gel (S) glass (G) delivers the modified materials (Z4, S7, G4, G5, G7, G8, etc.), can ions noble metal (Au, Rh, Pd: G4 + Au, G5 Pd, G7 Rh). Thus, synthesized Si-organic polymers turned out be promising sorbents (enterosorbents) noble, heavy, toxic applied in industry, environment, medicine.

Language: Английский

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Continuous synthesis of N, N-dicyanoethylaniline in microreactors: Reaction kinetics and process intensification

Chinese Journal of Chemical Engineering, Journal Year: 2024, Volume and Issue: 72, P. 95 - 105

Published: June 21, 2024

Language: Английский

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Michael Reaction of Enyne Derivatives of Meldrum's Acid in Water: Synthetic Approach for Creating a C–N/C–S Bonds inwith Low Reactive Nucleophiles

Tetrahedron, Journal Year: 2024, Volume and Issue: 169, P. 134369 - 134369

Published: Nov. 14, 2024

Language: Английский

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3-Aminopropyltrietoxysilane and –Silatrane in the Michael Aza-Reaction with Acrylates. Synthesis, Structure, and Properties of Adducts

Russian Journal of General Chemistry, Journal Year: 2023, Volume and Issue: 93(S1), P. S210 - S218

Published: Nov. 1, 2023

Language: Английский

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Pull-Pull Β-Oxo-Α- or Β-Haloenoates: A Toy for Theoreticians or Tool for Synthetics?

Published: Jan. 1, 2024

Language: Английский

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