Browse
Submit Data
Databases
API
Help

Dataset Information

41 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Asymmetric Synthesis of N-Substituted α-Amino Esters from α-Ketoesters via Imine Reductase-Catalyzed Reductive Amination.

ABSTRACT: N-Substituted α-amino esters are widely used as chiral intermediates in a range of pharmaceuticals. Here we report the enantioselective biocatalyic synthesis of N-substituted α-amino esters through the direct reductive coupling of α-ketoesters and amines employing sequence diverse metagenomic imine reductases (IREDs). Both enantiomers of N-substituted α-amino esters were obtained with high conversion and excellent enantioselectivity under mild reaction conditions. In addition >20 different preparative scale transformations were performed highlighting the scalability of this system.

SUBMITTER: Yao P

PROVIDER: S-EPMC8048798 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Synthesis of 2,3-Dialkylated Tartaric Acid Esters via Visible Light Photoredox-Catalyzed Reductive Dimerization of α-Ketoesters.

Project description:A mild transition-metal-free protocol to prepare 2,3-dialkylated tartaric acid esters has been developed by taking advantage of a visible light photoredox-catalyzed reductive dimerization of α-ketoesters with a combination of an organic dye photocatalyst and a Hantzsch-type 1,4-dihydropyridine hydrogen donor. A broad range of functional groups including cyclopropane, alkene, alkyne, 4-methoxybenzyl ether, acetal, silyl ether, carbamate, cyclic ether, cyclic thioether, bromoalkane, and N-alkoxyphthalimide are well-compatible. By employing the visible light photoredox-catalyzed reductive coupling and the subsequent optical resolution, both enantioenriched diastereomers of 2,3-dialkylated tartaric acid could be acquired conveniently.

| S-EPMC6641980 | biostudies-literature

Asymmetric synthesis of ?-branched amines via rhodium-catalyzed reductive amination.

Project description:Amines bearing ?-stereocenters are highly important structural motifs in many biologically active compounds. However, reported enantioselective syntheses of these molecules are indirect and often require multiple steps. Herein, we report a general asymmetric route for the one-pot synthesis of chiral ?-branched amines through the highly enantioselective isomerization of allylamines, followed by enamine exchange and subsequent chemoselective reduction. This protocol is suitable for establishing various tertiary stereocenters, including those containing dialkyl, diaryl, cyclic, trifluoromethyl, difluoromethyl, and silyl substituents, which allows for a rapid and modular synthesis of many chiral ?-branched amines. To demonstrate the synthetic utility, Terikalant and Tolterodine are synthesized using this method with high levels of enantioselectivity.

| S-EPMC5864842 | biostudies-other

Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters.

Project description:The synergistic use of chiral bifunctional ammonium iodide catalysts in combination with simple catalytically relevant aldimines allows for an unprecedented asymmetric α-hydroxylation reaction of β-ketoesters using H2O2. The reaction proceeds via in situ formation of a hypervalent iodine species, which then reacts with the used aldimine to generate an activated electrophilic oxygen transfer reagent.

| S-EPMC7418104 | biostudies-literature

DNA-catalyzed reductive amination.

Project description: Not available

| S-EPMC3269127 | biostudies-literature

Iridium-catalyzed direct asymmetric reductive amination utilizing primary alkyl amines as the N-sources.

Project description:Direct asymmetric reductive amination is one of the most efficient methods for the construction of chiral amines, in which the scope of the applicable amine coupling partners remains a significant challenge. In this study we describe primary alkyl amines effectively serve as the N-sources in direct asymmetric reductive amination catalyzed by the iridium precursor and sterically tunable chiral phosphoramidite ligands. The density functional theory studies of the reaction mechanism imply the alkyl amine substrates serve as a ligand of iridium strengthened by a (N)H-O(P) hydrogen-bonding attraction, and the hydride addition occurs via an outer-sphere transition state, in which the Cl-H H-bonding plays an important role. Through this concise procedure, cinacalcet, tecalcet, fendiline and many other related chiral amines have been synthesized in one single step with high yields and excellent enantioselectivity.

| S-EPMC9187633 | biostudies-literature

Asymmetric α-amination of β-keto esters using a guanidine-bisurea bifunctional organocatalyst.

Project description:An asymmetric α-amination of β-keto esters with azodicarboxylate in the presence of a guanidine-bisurea bifunctional organocatalyst was investigated. The α-amination products were obtained in up to 99% yield with up to 94% ee.

| S-EPMC4778535 | biostudies-literature

Phosphine-catalyzed asymmetric additions of malonate esters to {gamma}-substituted allenoates and allenamides.

Project description:Because carbonyl groups are ubiquitous in organic chemistry, the ability to synthesize functionalized carbonyl compounds, particularly enantioselectively, is an important objective. We have developed a straightforward and versatile method for catalytic asymmetric carbon-carbon bond formation at the ?-position of carbonyl compounds, specifically, phosphine-catalyzed additions of malonate esters to ?-substituted allenoates and allenamides. Mechanistic studies have provided insight into the reaction pathway.

| S-EPMC2996437 | biostudies-literature

CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids.

Project description:The direct enantioselective copper hydride (CuH)-catalyzed synthesis of β-chiral amides from α,β-unsaturated carboxylic acids and secondary amines under mild reaction conditions is reported. The method utilizes readily accessible carboxylic acids and tolerates a variety of functional groups in the β-position including several heteroarenes. A subsequent iridium-catalyzed reduction to γ-chiral amines can be performed in the same flask without purification of the intermediate amides.

| S-EPMC8027949 | biostudies-literature

Nickel-catalyzed asymmetric reductive arylation of α-chlorosulfones with aryl halides.

Project description:We report an asymmetric Ni-catalyzed reductive cross-coupling of aryl/heteroaryl halides with racemic α-chlorosulfones to afford enantioenriched sulfones. The reaction tolerates a variety of functional groups under mild reaction conditions, which complements the current methods. The utility of this work was demonstrated by facile late-stage functionalization of commercial drugs.

| S-EPMC8179603 | biostudies-literature

Catalytic asymmetric hydrogenation of (<i>Z</i>)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters.

Project description:The direct catalytic asymmetric hydrogenation of (Z)-α-dehydroamino boronate esters was realized. Using this approach, a class of therapeutically relevant alkyl-substituted α-amidoboronic esters was easily synthesized in high yields with generally excellent enantioselectivities (up to 99% yield and 99% ee). The utility of the products has been demonstrated by transformation to their corresponding boronic acid derivatives by a Pd-catalyzed borylation reaction and an efficient synthesis of a potential intermediate of bortezomib. The clean, atom-economic and environment friendly nature of this catalytic asymmetric hydrogenation process would make this approach a new alternative for the production of alkyl-substituted α-amidoboronic esters of great potential in the area of organic synthesis and medicinal chemistry.

| S-EPMC8146211 | 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