Browse
Submit Data
Databases
API
Help

Dataset Information

43 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Enantioselective PCCP Bronsted acid-catalyzed aminalization of aldehydes.

ABSTRACT: Here we present an enantioselective aminalization of aldehydes catalyzed by Brønsted acids based on pentacarboxycyclopentadienes (PCCPs). The cyclization reaction using readily available anthranilamides as building blocks provides access to valuable 2,3-dihydroquinazolinones containing one stereogenic carbon center with good enantioselectivity (ee up to 80%) and excellent yields (up to 97%).

SUBMITTER: Kamlar M

PROVIDER: S-EPMC8450961 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes.

Kamlar Martin M Reiberger Robert R Nigríni Martin M Císařová Ivana I Veselý Jan J

Beilstein journal of organic chemistry 20210916

Here we present an enantioselective aminalization of aldehydes catalyzed by Brønsted acids based on pentacarboxycyclopentadienes (PCCPs). The cyclization reaction using readily available anthranilamides as building blocks provides access to valuable 2,3-dihydroquinazolinones containing one stereogenic carbon center with good enantioselectivity (ee up to 80%) and excellent yields (up to 97%). ...[more]

PMID: 34621405

Similar Datasets

Chiral Bronsted acid-catalyzed allylboration of aldehydes.

Project description:The catalytic enantioselective allylation of aldehydes is a long-standing problem of considerable interest to the chemical community. We disclose a new high-yielding and highly enantioselective chiral Brønsted acid-catalyzed allylboration of aldehydes. The reaction is shown to be highly general, with a broad substrate scope that covers aryl, heteroaryl, alpha,beta-unsaturated, and aliphatic aldehydes. The reaction conditions are also shown to be effective for the catalytic enantioselective crotylation of aldehydes. We believe that the high reactivity of the allylboronate is due to protonation of the boronate oxygen by the chiral phosphoric acid catalyst.

| S-EPMC2928988 | biostudies-literature

Bronsted acid catalyzed asymmetric propargylation of aldehydes.

Project description: Not available

| S-EPMC3334334 | biostudies-literature

Enantioselective PCCP Bronsted acid-catalyzed aza-Piancatelli rearrangement.

Project description:An enantioselective aza-Piancatelli rearrangement has been developed using a chiral Brønsted acid based on pentacarboxycyclopentadiene (PCCP). This reaction provides rapid access to valuable chiral 4-amino-2-cyclopentenone building blocks from readily available starting material and is operationally simple.

| S-EPMC6633596 | biostudies-literature

Chiral Bronsted Acid Catalyzed Cascade Alcohol Deprotection and Enantioselective Cyclization.

Project description:The protection-deprotection sequence is vital to organic synthesis. Here, we describe a novel catalytic cascade where a chiral Brønsted acid selectively removes ether protecting groups and catalyzes intramolecular cyclization in one pot. We tested three model substrates from our previous work and investigated the rate of deprotection through gas chromatography (GC) studies. This work builds on our stereoselective synthesis of lactones by streamlining our synthesis. It also opens the door for additional investigations into other catalytic cascade reactions using chiral Brønsted acid catalysts.

| S-EPMC10795110 | biostudies-literature

Palladium(II)/Bronsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes.

Project description:An enantioselective oxidative carbocyclization-borylation of enallenes that is catalyzed by palladium(II) and a Brønsted acid was developed. Biphenol-type chiral phosphoric acids were superior co-catalysts for inducing the enantioselective cyclization. A number of chiral borylated carbocycles were synthesized in high enantiomeric excess.

| S-EPMC4471548 | biostudies-literature

Nickel/Bronsted Acid-Catalyzed Chemo- and Enantioselective Intermolecular Hydroamination of Conjugated Dienes.

Project description:A novel nickel/Brønsted acid-catalyzed asymmetric hydroamination of acyclic 1,3-dienes has been established. A wide array of primary and secondary amines can be transformed into allylic amines with high yields and high enantioselectivities under very mild conditions. Moreover, our method is compatible with various functional groups and heterocycles, allowing for late-stage functionalization of biologically active complex molecules. Remarkably, this protocol exhibits good chemoselectivity with respect to amines bearing two different nucleophilic sites. Mechanistic studies reveal that the enantioselective carbon-nitrogen bond-forming step is reversible.

| S-EPMC6906649 | biostudies-literature

Chiral Bronsted acid-catalysed enantioselective allylboration of sterically hindered aldehydes enabled by multiple hydrogen bonding interactions.

Project description:Chiral phosphoric acids (CPAs) are an important class of chiral Brønsted acid catalysts that can accomplish highly effective enantioselective allylborations of aldehydes. However, traditional CPA-catalysed allyboration has difficulty utilizing sterically hindered aldehydes, where the corresponding products of enantioenriched secondary alcohols adjacent to a quaternary carbon are important moieties in biologically active natural products. To overcome this issue, we employed a chiral phosphoramide catalyst for allylation and crotylation reactions of the allyl boronic acid pinacol ester with sterically hindered aldehydes to benefit from multiple hydrogen bonding interactions between the chiral phosphoramide and substrates. As a result, not only the sterically hindered aldehydes, but the less sterically hindered ones, could also be subjected to enantioselective allylboration using the chiral phosphoramide catalyst by "interaction strategy". Indeed, conventional CPAs were ineffective for the reactions presented here, resulting in low conversions and enantioselectivities. Computational studies revealed that the most stable transition state comprises weak attractive interactions between phosphoramide and substrates. These interactions did not exist in traditional allylborations with chiral phosphoric acids. In conclusion, the sum of weak interactions, including S[double bond, length as m-dash]O⋯H-C and two C-F⋯H-C hydrogen bonding interactions, substantially impacts the enantioselectivity of the allylboration of sterically hindered aldehydes.

| S-EPMC11817098 | biostudies-literature

Enantioselective addition of boronates to chromene acetals catalyzed by a chiral Bronsted acid/Lewis acid system.

Project description: Not available

| S-EPMC3035997 | biostudies-literature

Chiral Pentacarboxycyclopentadiene-Based Bronsted Acid-Catalyzed Enantioselective Desymmetrization of Meso-Epoxides by 2-Mercaptobenzothiazoles.

Project description:Enantioselective desymmetrization of meso-epoxides by 2-mercaptobenzothiazoles was realized by using the pentacarboxycyclopentadiene-based chiral Brønsted acid in combination of N-isopropylaniline as amine additive to give up to 90.5:9.5 er of the ring opening products.

| S-EPMC6644688 | biostudies-literature

Enantioenriched 1,4-Benzoxazepines via Chiral Bronsted Acid-Catalyzed Enantioselective Desymmetrization of 3-Substituted Oxetanes.

Project description:Herein, we present a highly enantioselective desymmetrization of 3-substituted oxetanes enabled by a confined chiral phosphoric acid. This metal-free process allows effective access to chiral seven-membered 1,4-benzoxazepines with a high degree of enantiocontrol, under mild reaction conditions. The developed synthetic strategy tolerates a broad substrate scope and demonstrates its synthetic utility in various enantioselective product transformations, thus proving its effectiveness in diverse scenarios.

| S-EPMC10729023 | 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