Introduction of a Tropine-based Dicationic Catalyst for the N-Boc Protection and Acetylation of Amines under Solvent-free Conditions.

Autor: Pourdasht, S., Mousapour, M., Shirini, F., Tajik, H.
Předmět:
Zdroj: Organic Preparations & Procedures International; 2024, Vol. 56 Issue 4, p392-401, 10p
Abstrakt: This article discusses the importance of protecting amines in organic synthesis to prevent unwanted side reactions, particularly in the synthesis of complex peptides, amino acids, and natural products. Various methods for amine protection are explored, including formylation, acetylation, alkylation, and the use of specific groups like Boc, Cbz, and Fmoc. The article introduces a new dicationic catalyst, [C4(Tr)2]·2Cl, for the N-Boc protection and acetylation of amines under solvent-free conditions. The catalyst is shown to be effective in producing N-tert-butylcarbamates and N-acetamides with high yields and minimal variation based on substituents. The method is selective and does not damage structural units like the methoxy group. The efficiency of this method is compared to other reported methods and is shown to have favorable reaction times, yields, and mild conditions. The catalyst is easily prepared, reusable, and environmentally friendly. The article provides detailed experimental procedures and characterization data for the catalyst and the synthesized compounds. The authors hope that this new catalyst will find further applications in synthesis. [Extracted from the article]
Databáze: Complementary Index