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Relevant academic research and scientific papers

Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by rare-earth metal amides RE[N(SiMe3)2]3with chiral TADDOL ligands

The catalytic asymmetric epoxidation of α,β-unsaturated ketones by tert-butylhydroperoxide (TBHP) has been well established using rare-earth metal amides RE[N(SiMe3)2]3 (RE = La(1), Nd(2), Sm(3), Y(4), Yb(5)) with chiral TADDOL ligands. It was found that

Asymmetric Epoxidation of Enones Promoted by Dinuclear Magnesium Catalyst

Asymmetric synthesis with cheaper and non-toxic alkaline earth metal catalysts is becoming an important and sustainable alternative to conventional catalytic methodologies mostly relying on precious metals. In spite of some sustainable methods for enantioselective epoxidation of enones, the development of a well-defined and efficient catalyst based on magnesium complexes for these reactions is still a challenging task. In this perspective, we present the application of chiral dinuclear magnesium complexes for asymmetric epoxidation of a broad range of electron-deficient enones. We demonstrate that the in situ generated magnesium-ProPhenol complex affords enantioenriched oxiranes in high yields and with excellent enantioselectivities (up to 99% ee). Our extensive study verifies the literature data in this area and provides a step forward to better understand the factors controlling the oxygenation process. Elaborated catalyst offers mild reaction conditions and a truly wide substrate scope. (Figure presented.).

Application of chiral TADDOL ligand and rare earth metal amide in combined catalysis of asymmetric reaction

The invention relates to application of chiral TADDOL ligand and rare earth metal amide in combined catalysis of asymmetric epoxidation reaction of chalcone compounds. According to the application, alpha, beta-unsaturated ketone shown in a formula (1) and tert-butyl hydroperoxide react in the presence of organic alkali under the combined catalytic action of a chiral TADDOL ligand shown in a formula (3) and rare earth metal amide in an anhydrous, oxygen-free and protective atmosphere to obtain the chiral epoxy compound shown in the formula (2) after the reaction is completed, wherein R1 is selected from hydrogen, alkyl, halogen, alkoxy, trifluoromethyl, nitro or cyano, R2 is selected from phenyl, substituted phenyl, naphthyl, furyl or thienyl; R3 and R4 are respectively and independently selected from alkyl, phenyl or R3 and R4 and carbon atoms connected with R3 and R4 form naphthenic base; Ar is phenyl, substituted phenyl, biphenyl or naphthyl; the molecular formula of the rare earth metal amide is RE [N (SiMe3) 2] 3. The method has the advantages of wide substrate application range, high yield and high enantioselectivity.

The Synthesis of Hydrobenzoin-Based Monoaza Crown Ethers and Their Application as Recyclable Enantioselective Catalysts

Abstract: New recyclable monoaza-15-crown ethers have been synthesized starting from (R,R)-(+)- and (S,S)-(?)-hydrobenzoin. These macrocycles proved to be efficient and reusable phase transfer catalysts in a few asymmetric reactions under mild conditions.

Crown-ether-modified cyclic dipeptides as supramolecular chiral catalysts

With the objective to develop supramolecular catalysts for useful chemical transformations, we report here a rapid and efficient solid-phase synthesis of novel cyclic dipeptides (crown-CDPs) with a diversity of L-DOPA derived crown ether substituents and

Chiral calcium-catalyzed asymmetric epoxidation reactions using hydrogen peroxide as the terminal oxidant

Asymmetric epoxidation reactions of chalcone derivatives catalyzed by chiral calcium complexes using hydrogen peroxide were developed. The epoxidation reactions proceeded smoothly to afford the desired products in good yields with good enantioselectivitie

Revisiting the Juliá-Colonna enantioselective epoxidation: Supramolecular catalysis in water

We describe an efficient epoxidation process leading to chiral epoxyketones using the reusable homo-oligopeptide poly-l-leucine (PLL) in pure water, without any organic co-solvent. A range of substituted epoxyketones can be accessed with good conversions and high enantioselectivities. Based on the experimental results and computational studies, we propose a mechanism that demonstrates the importance of both the α-helical structure and the presence of a hydrophobic groove of the homo-oligopeptide catalyst for reactivity and selectivity.

Asymmetric Cascade Catalysis with Chiral Polyoxometalate-Based Frameworks: Sequential Direct Aldol and Epoxidation Reactions

Catalytic asymmetric cascade reactions in which the substrates are transferred through well-choreographed consecutive independent steps by a single catalyst have received increasing interest. By incorporating a chiral organocatalyst pyrrolidine, an oxidat

Highly selective multifunctional nanohybrid catalysts for the one-pot synthesis of α,β-epoxy-chalcones

An efficient one-pot heterogeneous process for producing chiral α,β-epoxy-chalcones from the corresponding aldehydes and ketones has been described. The nanohybrid materials based on poly-l-leucine immobilised into rehydrated hydrotalcites did not require any pre-activation and were easily recovered and recycled for four consecutive runs without losing their catalytic efficiency in terms of conversion, total selectivity towards the corresponding epoxy-chalcones and excellent enantioselectivity.

Biomimetic epoxidation in aqueous media catalyzed by cyclic dipeptides

We have developed a practical epoxidation of electron-deficient enones in aqueous media using cyclic dipeptides as bioinspired green catalyst. Optimizing the reaction conditions in a triphasic system led to efficient conditions providing epoxides with good enantioselectivities. Depending on the catalyst substituent chirality, both enantiomers are obtained. The cyclic rigidity impacts significantly the enantioselectivity.