• Issue

    European Journal of Organic Chemistry: Volume 27, Issue 39

    October 14, 2024

Cover

Free Access

Front Cover: Unleashing the Power of Domino Reactions on Carbohydrates: State of the Art (Eur. J. Org. Chem. 39/2024)

  • First Published: 21 October 2024

Front Cover: Unleashing the Power of Domino Reactions on Carbohydrates: State of the Art (Eur. J. Org. Chem. 39/2024) Volume 27 Issue 39, 2024

The Front Cover shows domino transformations, which play a crucial role as chemical tools in drug discovery processes. In their Review (DOI: 10.1002/ejoc.202400511), S. Mazzotta, G. D'Orazio and co-workers showcase various instances of domino transformations applied to carbohydrates, with the goal of summarizing their chemical potential in producing sugar-derived compounds. These compounds have significant applications in generating new chemical scaffolds for drug discovery and chemical biology.

Review

Open Access

Unleashing the Power of Domino Reactions on Carbohydrates: State of the Art

  • First Published: 10 August 2024

Unleashing the Power of Domino Reactions on Carbohydrates: State of the Art

Domino transformations play a crucial role as chemical tools in drug discovery processes. This review showcases various instances of domino transformations applied to carbohydrates, with the goal of summarizing their chemical potential in producing sugar-derived compounds. These compounds have significant applications in generating new chemical scaffolds for drug discovery and chemical biology.

Electrochemical Construction of C−F Bonds: Recent Advances and Future Perspectives

  • First Published: 09 August 2024
Electrochemical Construction of C−F Bonds: Recent Advances and Future Perspectives

Electro-organic synthesis, evolved as a sustainable and scalable approach in fluoriation chemistry, received rapid development recently. As a result, many novel and attracting applications of introduction of fluorine atoms into organic compounds by direct and redox-mediated electrochemical methods has been reported, especially in recent five years. In this review, the reaction scopes, reaction mechanism, the fundamental aspects and the fluorine source variation in electrochemcial fluoriation transformation are highlighted.

Synthesis, Structure and Properties of Core-Modified Calixporphyrinoids

  • First Published: 16 July 2024
Synthesis, Structure and Properties of Core-Modified Calixporphyrinoids

Synthesis, structure, coordination, spectroscopic properties and applications of core-modified calix(n)phyrins that are resulted by replacing one or more pyrrole rings of calix(n)phyrins with different heterocycles such as thiophene, selenophene, tellurophene, phosphole, silole and so on and carbacycles such as m-/p-phenylene rings are described in this review.

One-Pot Double Cyclizations Involving an Aza-Prins Process

  • First Published: 14 July 2024
One-Pot Double Cyclizations Involving an Aza-Prins Process

In this review are discussed one-pot domino/cascade/tandem bis-cyclizations involving an aza-Prins process, for poly azacycles synthesis. Those are fused, bridged or spiranic depending on the position of the nucleophile. The mechanism of the two steps together with the stereochemical outcomes are detailed.

Perspective

Open Access

Non-Reductive CO2 Valorization into Oxazolidinones via Cycloaddition to Aziridines: A Personal Insight

  • First Published: 23 August 2024
Non-Reductive CO2 Valorization into Oxazolidinones via Cycloaddition to Aziridines: A Personal Insight

This perspective provides an overview of recent homogeneous and heterogeneous catalytic methodologies published on the CO2 cycloaddition to aziridines to form oxazolidinones, with a particular attention to the employed experimental conditions, which are essential parameters for envisioning real costs and possible applications of these synthetic processes.

Research Article

Very Important Paper

Open Access

2-Methylene-1,2-dihydropyridines (2-pyNHOs): Highly Nucleophilic Enamines

  • First Published: 30 April 2024
2-Methylene-1,2-dihydropyridines (2-pyNHOs): Highly Nucleophilic Enamines

2-Methylene-1,2-dihydropyridines (2-pyNHOs) are enamines with strongly polarized exocyclic π-bond. The 2-pyNHOs react with quinone methides to give zwitterionic adducts or the entirely neutral adduct tautomers. The kinetics of 2-pyNHO/electrophile reactions were studied and evaluated by the Mayr-Patz equation. With nucleophilicities N from 19.4 to 21.2, 2-pyNHOs are significantly more reactive than classical enamines.

FeCl3 Catalyzed Synthesis of cis-Fused Reduced THC Analogues

  • First Published: 25 July 2024
FeCl3 Catalyzed Synthesis of cis-Fused Reduced THC Analogues

FeCl3 catalyzes the isomerization of 2-prenylated-2H-pyrans towards cis-fused tetrahydro-6H-benzo[c]chromene systems (cis-THC analogues). The same catalyst promotes the formation of these products via cyclocondensation of 1,3-dicarbonyl substrates and citral/farnesal-type aldehydes. The synthetic strategy could be applied to the racemic preparation of biologically relevant natural products cis-perrottetinene and Δ9-cis-tetrahydrocannabiorcol.

Enantioselective Synthesis of Axially Chiral Heterobiaryl N-Cbz-Protected Diamines via Organocatalytic Arylation of 5-Aminoisoxazoles

  • First Published: 08 June 2024
Enantioselective Synthesis of Axially Chiral Heterobiaryl N-Cbz-Protected Diamines via Organocatalytic Arylation of 5-Aminoisoxazoles

Axially chiral arylisoxazoles with high yields (up to 96 %) and excellent enantiomeric purities (up to 97 % ee) were synthesized through organocatalytic arylation of isoxazoles with N-Cbz-protected azonaphthalenes. Cbz protecting group can be readily removed, resulting in axially chiral heterobiaryl amines bearing free amine maintaining enantiomeric purity.

Open Access

A Concise Ring Closing Enyne Metathesis Approach for the Preparation of Functionalized Proline-Derived Azabicycloalkane Amino Acids

  • First Published: 08 July 2024
A Concise Ring Closing Enyne Metathesis Approach for the Preparation of Functionalized Proline-Derived Azabicycloalkane Amino Acids

Constrained C4-functionalized dipeptide derivatives incorporating a proline moiety were prepared in high yields by exploiting a direct ring closing enyne metathesis (RCEYM) reaction. Post-functionalization studies of the newly introduced diene system pave the way for future applications in peptide synthesis, medicinal chemistry and nanotechnology.

Reduction and Hydrocyanation of Aziridines with C−C Bond Cleavage

  • First Published: 29 June 2024
Reduction and Hydrocyanation of Aziridines with C−C Bond Cleavage

Unusual CC bond cleavage of 2,3-diaryl aziridines took place to afford secondary amines by formal dihydrogenation and hydrocyanation. Formal dehydrogenation was performed by electrocyclic ring opening of N-Li or N-Na aziridines to azaallyl anions followed by reduction with NaBH4. Formal hydrocyanation was realized by treating azaallyl anions with Me3SiCN.

Open Access

Chemoselective Synthesis of Cyanoformamides from Isocyanates and a Highly Reactive Nitrile Anion Reservoir

  • First Published: 10 July 2024
Chemoselective Synthesis of Cyanoformamides from Isocyanates and a Highly Reactive Nitrile Anion Reservoir

A chemoselective preparation of cyanoformamides from widely available isocyanates and a reactive silyl cyanide–as the competent nucleophilic CN anion – is reported. The methodology requires the use of a suitable Lewis base (potassium tert-pentoxide) for the proper activation of the cyanide donor.

Room Temperature Ni-Catalyzed Ullmann Reaction of (Hetero)aryl/Vinyl Chlorides Enabled by Silylchloride-Activated Mn Powders

  • First Published: 24 July 2024
Room Temperature Ni-Catalyzed Ullmann Reaction of (Hetero)aryl/Vinyl Chlorides Enabled by Silylchloride-Activated Mn Powders

Pre-activation of Mn powers by trimethylsilylchloride (TMSCl) enables a highly efficient Ni-catalyzed reductive homocoupling of (hetero)aryl/vinyl chlorides in DMA at room temperature to afford symmetrical biaryls/dienes in good to excellent yields although TMSCl plays a double-face role, activating Mn but deactivating Ni catalyst.