Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen

ABSTRACT:

SUBMITTER:

PROVIDER: S-EPMC10682516 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Short, enantioselective, gram-scale synthesis of (-)-zephyranthine.

Project description:A reasonable synthesis design by strategically integrating functional group manipulation into the ring system construction resulted in a short, enantioselective, gram-scale total synthesis of (-)-zephyranthine. The concise route includes a catalytic Michael/Michael cascade for the asymmetric synthesis of a penta-substituted cyclohexane with three contiguous stereogenic centers, a remarkable 8-step one-pot operation to easily assemble the zephyranthine tetracyclic skeleton, the regioselective construction of a double bond in the C ring and an asymmetric dihydroxylation. This synthesis is also flexible and paves a potential path to a variety of cyclohexylamine-fused tricyclic or polycyclic alkaloids.

| S-EPMC8278928 | biostudies-literature

Enantioselective small molecule synthesis by carbon dioxide fixation using a dual Bronsted acid/base organocatalyst.

Project description:Carbon dioxide exhibits many of the qualities of an ideal reagent: it is nontoxic, plentiful, and inexpensive. Unlike other gaseous reagents, however, it has found limited use in enantioselective synthesis. Moreover, unprecedented is a tool that merges one of the simplest biological approaches to catalysis-Brønsted acid/base activation-with this abundant reagent. We describe a metal-free small molecule catalyst that achieves the three component reaction between a homoallylic alcohol, carbon dioxide, and an electrophilic source of iodine. Cyclic carbonates are formed enantioselectively.

| S-EPMC4708058 | biostudies-literature

Multi-gram scale synthesis of FR180204.

Project description:A concise synthesis of the ERK inhibitor FR180204 has been developed. The synthesis consists of six operationally simple steps and can be utilized to make multi-gram quantities of FR180204.

| S-EPMC2862695 | biostudies-literature

Synthesis and Stereochemical Characterization of a Novel Chiral α-Tetrazole Binaphthylazepine Organocatalyst.

Project description:A novel α-tetrazole-substituted 1,1'-binaphthylazepine chiral catalyst has been synthesized and its absolute configuration has been determined by DFT computational analysis of the vibrational circular dichroism (VCD) spectrum of its precursor. The VCD analysis, carried out through the model averaging method, allowed to assign the absolute configuration of a benzylic stereocenter in the presence of a chiral binaphthyl moiety. The 1,1'-binaphthylazepine tetrazole and the nitrile its immediate synthetic precursor, have been preliminarily tested as chiral organocatalysts in the asymmetric intramolecular oxa-Michael cyclization of 2-hydroxy chalcones for the synthesis of chiral flavanones obtaining low enantioselectivity.

| S-EPMC9413694 | biostudies-literature

Thermo-responsive chiral micelles as recyclable organocatalyst for asymmetric Rauhut-Currier reaction in water.

Project description:Developing eco-friendly chiral organocatalysts with the combined advantages of homogeneous catalysis and heterogeneous processes is greatly desired. In this work, a family of amphiphilic one-handed helical polyisocyanides bearing phosphine pendants is prepared, which self-assembles into well-defined chiral micelles in water and showed thermo-responsiveness with a cloud point of approximately 38.4 °C. The micelles with abundant phosphine moieties at the interior efficiently catalyze asymmetric cross Rauhut-Currier reaction in water. Various water-insoluble substrates are transferred to target products in high yield with excellent enantioselectivity. The yield and enantiomeric excess (ee) of the product generated in water are up to 90% and 96%, respectively. Meanwhile, the yields of the same R-C reaction catalyzed by the polymer itself in organic solvents is <16%, with an ee < 72%. The homogeneous reaction of the chiral micelles in water turns to heterogeneous at temperatures higher than the cloud point, and the catalyst precipitation facilitates product isolation and catalyst recovery. The polymer catalyst is recycled 10 times while maintaining activity and enantioselectivity.

| S-EPMC10638429 | biostudies-literature

Chitosan-EDTA-Cellulose network as a green, recyclable and multifunctional biopolymeric organocatalyst for the one-pot synthesis of 2-amino-4H-pyran derivatives.

Project description:In this research, cellulose grafted to chitosan by EDTA (Cs-EDTA-Cell) bio-based material is reported and characterized by a series of various methods and techniques such as FTIR, DRS-UV-Vis, TGA, FESEM, XRD and EDX analysis. In fact, the Cs-EDTA-Cell network is more thermally stable than pristine cellulose or chitosan. There is a plenty of both acidic and basic sites on the surface of this bio-based and biodegradable network, as a multifunctional organocatalyst, to proceed three-component synthesis of 2-amino-4H-pyran derivatives at room temperature in EtOH. The Cs-EDTA-Cell nanocatalyst can be easily recovered from the reaction mixture by using filtration and reused for at least five times without significant decrease in its catalytic activity. In general, the Cs-EDTA-Cell network, as a heterogeneous catalyst, demonstrated excellent catalytic activity in an environmentally-benign solvent to afford desired products in short reaction times and required simple experimental and work-up procedure compared to many protocols using similar catalytic systems.

| S-EPMC9126885 | biostudies-literature

Synthesis and Applications of Cinchona Squaramide-Modified Poly(Glycidyl Methacrylate) Microspheres as Recyclable Polymer-Grafted Enantioselective Organocatalysts.

Project description:This work presents the immobilization of cinchona squaramide organocatalysts on poly(glycidyl methacrylate) solid supports. Preparation of the well-defined monodisperse polymer microspheres was facilitated by comprehensive parameter optimization. By exploiting the reactive epoxy groups of the polymer support, three amino-functionalized cinchona derivatives were immobilized on this carrier. To explore the effect of the amino linker, these structurally varied precatalysts were synthesized by modifying the cinchona skeleton at different positions. The catalytic activities of the immobilized organocatalysts were tested in the Michael addition of pentane-2,4-dione and trans-β-nitrostyrene with excellent yields (up to 98 %) and enantioselectivities (up to 96 % ee). Finally, the catalysts were easily recovered five times by centrifugation without loss of activity.

| S-EPMC7702047 | biostudies-literature

Recyclable photocatalyst perovskite as a single-electron redox mediator for visible-light-driven photocatalysis gram-scale synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones in air atmosphere.

Project description:Based on the Biginelli reaction of β-ketoesters, arylaldehydes, and urea/thiourea, we created a green radical synthesis procedure for 3,4-dihydropyrimidin-2-(1H)-ones/thiones. A single-electron redox mediator was applied to a solution of ethanol in an air environment, at room temperature, and with blue LEDs as a renewable energy source in order to create. The objective of this research is to create a halide perovskite that is widely available, affordable, recyclable, and economically feasible. A factor mentioned in the discussion is that the procedure tolerates a variety of donating and withdrawing functional groups while still offering a very fast rate and excellent yields. The range of yields is quite uniform (86-94%, average: 90.4%), and the range of reaction times is very quick (4-8 min, average: 5.8 min). Furthermore, gram-scale cyclization shows that it is applicable for use in industry. Additionally, CsPbBr3 is quite stable and can be used six times in a row without experiencing significant structural changes or activity loss, which has been extremely helpful in meeting industrial needs and environmental issues.

| S-EPMC10290714 | biostudies-literature

Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production.

Project description:The preparation of novel multi-substituted 1,2,3-triazole-modified β-aminocyclohexanecarboxylic acid derivatives in a simple and efficient continuous-flow procedure is reported. The 1,3-dipolar cycloaddition reactions were performed with copper powder as a readily accessible Cu(I) source. Initially, high reaction rates were achieved under high-pressure/high-temperature conditions. Subsequently, the reaction temperature was lowered to room temperature by the joint use of both basic and acidic additives to improve the safety of the synthesis, as azides were to be handled as unstable reactants. Scale-up experiments were also performed, which led to the achievement of gram-scale production in a safe and straightforward way. The obtained 1,2,3-triazole-substituted β-aminocyclohexanecarboxylates can be regarded as interesting precursors for drugs with possible biological effects.

| S-EPMC3740622 | biostudies-literature

Gram-Scale Synthesis of a Bench-Stable 5,5″-Unsubstituted Terpyrrole.

Project description:The controlled preparation of higher order oligopyrrolic species holds broad utility across the chemical and material sciences. Here, we describe the gram-scale synthesis of a bench-stable 5,5″-unsubstituted terpyrrole in excellent yield via a tandem Suzuki cross-coupling with in situ deprotection. The solution and solid-state stability as well as UV-vis, fluorescence, and single crystal X-ray diffraction structure are also detailed.

| S-EPMC6381930 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data