Unnatural Cyclopeptide Synthesis via Cu-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides DOI

Enrique Gallent,

Inés Alonso, Juan C. Carretero

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 19, 2024

Cyclic peptides are valued synthetic targets in organic and medicinal chemistry. Herein, we report an efficient strategy for the synthesis of unnatural cyclic via Cu-catalyzed 1,3-dipolar cycloaddition azomethylene ylides. Linear precursors different lengths bearing diverse amino acids (26 examples) shown to be compatible with this method, affording good yields complete endo-diastereoselectivities. Density functional theory (DFT) calculations support a stepwise mechanism which Cu plays key role preorganization reactants.

Language: Английский

Tandem Synthesis of Polysubstituted Pyrroles via Cu(I)-Catalyzed Cyclization of Ketene N,S-Acetals with β-Ketodinitriles DOI
Anup Sharma,

Mahesh Kumar,

Shiv Chand

et al.

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

Published: March 11, 2025

A new approach to multifunctionalized pyrroles has been explored by the tandem cyclization of α-oxoketene-N,S-acetals with β-ketodinitriles using Cu(MeCN)4BF4 and Ag2CO3 in toluene under reflux conditions. The reaction involves C–C/C–N bond creation, is assumed proceed via enamine formation, intramolecular cyclization, rearrangement. potential methodology also demonstrated for a gram-scale as well some useful organic transformations. offers practical pathway achieve polysubstituted broad substrate scope good functional group tolerance.

Language: Английский

Citations

0
Peptide Macrocyclization via Cu-catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides DOI Creative Commons
Javier Adrio, Nuria Rodríguez, Juan C. Carretero

et al.

Published: June 25, 2024

Cyclic peptides are highly valued synthetic targets in organic and medicinal chemistry. The development of new methodologies for peptide macrocyclization, different from classical lactamization, is essential the progress field. Herein, we report an efficient diastereoselective macrocyclization strategy synthesis cyclic using 1,3-dipolar cycloaddition azomethine ylides. Linear precursors length bearing diverse amino acids have shown to be compatible with this method (26 examples), giving good yields almost complete diastereoselectivity. DFT calculations suggest a stepwise mechanism which Cu plays key role reagents preorganization.

Language: Английский

Citations

2
Peptide Macrocyclization via Cu-catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides DOI Creative Commons
Javier Adrio, Nuria Rodríguez, Juan C. Carretero

et al.

Published: June 20, 2024

Cyclic peptides are highly valued synthetic targets in organic and medicinal chemistry. The development of new methodologies for peptide macrocyclization, different from classical lactamization, is essential the progress field. Herein, we report an efficient diastereoselective macrocyclization strategy synthesis cyclic using 1,3-dipolar cycloaddition azomethine ylides. Linear precursors length bearing diverse amino acids have shown to be compatible with this method (26 examples), giving good yields almost complete diastereoselectivity. DFT calculations suggest a stepwise mechanism which Cu plays key role reagents preorganization.

Language: Английский

Citations

1
Recent Advances for the Transformation of Maleimides via Annulation DOI
Mohammad Aslam, Muhammad Saeed Akhtar, Hee Nam Lim

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

This review highlights recent advances in maleimide-based annulation and cyclization strategies, offering insights into their synthetic versatility potential applications creating structurally diverse aromatics bioactive heterocycles.

Language: Английский

Citations

1
Unnatural Cyclopeptide Synthesis via Cu-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides DOI

Enrique Gallent,

Inés Alonso, Juan C. Carretero

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 19, 2024

Cyclic peptides are valued synthetic targets in organic and medicinal chemistry. Herein, we report an efficient strategy for the synthesis of unnatural cyclic via Cu-catalyzed 1,3-dipolar cycloaddition azomethylene ylides. Linear precursors different lengths bearing diverse amino acids (26 examples) shown to be compatible with this method, affording good yields complete endo-diastereoselectivities. Density functional theory (DFT) calculations support a stepwise mechanism which Cu plays key role preorganization reactants.

Language: Английский

Citations

1