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Relevant academic research and scientific papers

Aqueous asymmetric aldol reaction catalyzed by nanomagnetic solid acid SO42-/Zr(OH)4-Fe3O4

Magnetic solid acid catalysts SO42-/Zr(OH)4-Fe3O4 were prepared using magnetic Fe3O4 nanoparticles, ZrOCl2·8H2O, and sulfuric acid as starting materials in

Biocatalytic direct asymmetric aldol reaction using proteinase from Aspergillus melleus

The direct asymmetric aldol reaction of aromatic aldehydes with cyclic or acyclic ketones was catalyzed by proteinase from Aspergillus melleus (AMP) in acetonitrile in the presence of water. A wide range of substrates could be transformed into the corresp

Preparation of prolinamide with adamantane for aldol reaction catalysis in brine and separation using a poly(AN-MA-β-CD) nanofibrous film via host-guest interaction

Prolinamides with double-H potential were prepared and employed as organocatalysts in asymmetric aldol reactions. The catalyst with adamantane showed improved catalytic activity, which was further enhanced by using brine as the solvent. A series of aldol

Prolinamides of Aminouracils, Organocatalyst Modifiable by Complementary Modules

We report the synthesis and evaluation of prolinamide organocatalysts that incorporate aminouracils. The features of these catalysts are enhanced NH acidity of the amide because of the electron-withdrawing nature of the heterocycle, an additional hydrogen-bond donor at the α or β positions of this functional group (using 6-aminouracil or 5,6-diaminouracil respectively), and it can be recovered due to its low solubility and used again without decreasing the enantioselectivity. A unique feature of these systems is the self-assembly capability with complementary modules by Watson–Crick interactions. These supramolecular adducts behave differently from the catalyst alone, some of them have lower performance but others improve the selectivity of the product. Therefore, this approach avoids the synthesis of many catalysts.

Combining prolinamides with 2-pyrrolidinone: Novel organocatalysts for the asymmetric aldol reaction

Peptides and especially prolinamides have been identified as excellent organocatalysts for the aldol reaction. The combination of prolinamides with derivatives bearing the 2-pyrrolidinone scaffold, deriving from pyroglutamic acid, led to the identification of novel organocatalysts for the intermolecular asymmetric aldol reaction. The new hybrids were tested both in organic and aqueous media. Among the compounds tested, 22 afforded the best results in petroleum ether, while 25 afforded the products in brine in high yields and selectivities. Then, various ketones and aldehydes were utilized and the products of the aldol reaction were obtained in high yields (up to 100%) with excellent diastereo- (up to 97:3 dr) and enantioselectivities (up to 99% ee).

Proline dipeptides containing fluorine moieties as oganocatalysts for the asymmetric aldol reaction

A series of dipeptide analogues consisting of proline, phenylalanine and aniline- or phenol-fluorine derivatives were synthesized. Their catalytic ability was evaluated in the intermolecular asymmetric aldol reaction, both in organic and aqueous media. Aniline-fluorine derivatives proved to be superior and the best results were obtained, when 2-CF3 aniline was employed. A diverse substrate scope consisting of both aromatic and aliphatic aldehydes, as well as different ketones was demonstrated, where aromatic aldehydes afforded products in high yields (up to 100%) with excellent diastereo- (up to 95:5) and enantioselectivities (up to 97%), whereas the aliphatic aldehydes afforded also excellent selectivities, but relatively low yield. A simple addition of fluorine to a dipeptide analogue affords organocatalysts with new interesting properties that can catalyze the aldol reaction more efficiently.

A phosphotungstic acid-supported multifunctional organocatalyst containing 9-amino(9-deoxy): Epi -cinchonidine and Br?nsted acid and its application in asymmetric aldol reaction

A novel type of supported multifunctional organocatalyst CDNH2(n)-HPW combined 9-amino(9-deoxy)epi-cinchonidine (CDNH2) with Br?nsted acid in the backbone of phosphotungstic acid was developed via facile precipitation of sodium tungs

Tert-Butyl esters of peptides as organocatalysts for the asymmetric aldol reaction

Enantioselective aldol reactions between ketones and aldehydes were shown to be catalysed by a variety of tert-butyl esters of peptides. Amongst the peptides tested, Pro-Glu(OtBu)-OtBu proved to be the best, affording the product in

An Acid/Base-Regulated Recyclable Strategy for Homogeneous Cinchona Alkaloid-Derived Primary Amine Organocatalysts in Aldol, Vinylogous Michael and Double-Michael Cascade Reactions

A practical, recyclable strategy for homogeneous cinchona alkaloid-derived primary amine organocatalysts was developed by controlling the solubilities in an aqueous/organic biphasic system through regulating the pH of the aqueous phase, effecting the prot

Tert-Butyl esters of tripeptides based on Pro-Phe as organocatalysts for the asymmetric aldol reaction in aqueous or organic medium

The enantioselective aldol reaction between ketones and aldehydes constitutes one the most common reaction models for the evaluation of novel organocatalysts. The last few years, it has been shown that the organocatalytic aldol reaction can be performed i