Browse
Submit Data
Databases
API
Help

Dataset Information

33 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Cu(I)-catalyzed direct addition and asymmetric addition of terminal alkynes to imines.

ABSTRACT: A Cu(I)-catalyzed direct addition of alkynes to imines was developed. The process is simple and provides a diverse range of propargylamines in high enantiomeric excess and good yield both in water and in toluene. The absolute configuration of such addition products has been determined by x-ray crystallography.

SUBMITTER: Wei C

PROVIDER: S-EPMC395979 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Rhodium-catalyzed synthesis of branched amines by direct addition of benzamides to imines.

Project description:Rhodium-catalyzed addition of benzamide C-H bonds to a range of aromatic N-sulfonyl aldimines has been developed and proceeds with high functional group compatibility. The synthetic utility of the resulting branched amine products has also been demonstrated by the preparation of isoindoline and isoindolinone frameworks.

| S-EPMC3345069 | biostudies-literature

Direct Zinc(II)-Catalyzed Enantioconvergent Additions of Terminal Alkynes to ?-Keto Esters.

Project description:The addition of terminal alkynes to racemic ?-stereogenic ?-keto esters was achieved in high levels of stereoselectivity, affording versatile tertiary propargylic alcohols containing two stereocenters. This environmentally benign enantioconvergent reaction proceeds with perfect atom economy, requires no solvent, and is catalyzed by a non-toxic zinc salt. The alkyne moiety can be leveraged in downstream transformations including hydrogenation to the corresponding saturated tertiary alcohol, which represents the product of a formal enantioconvergent aliphatic nucleophile addition.

| S-EPMC5554871 | biostudies-literature

Vanadium-catalyzed addition of propargyl alcohols and imines.

Project description:A Mannich-type addition of propargylic alcohols and N-methoxycarbonylimines has been achieved by using a vanadium catalyst. The reactivity of the vanadium catalyst could be modulated by modifying the silanol ligands to avoid the background reaction. The strategy described herein provides an atom-economical access to beta-aryl-substituted Z-enones with an allylic amino functional group, which are not readily accessible with other methods.

| S-EPMC2529155 | biostudies-literature

Cu-Catalyzed Transannulation Reaction of Pyridotriazoles with Terminal Alkynes under Aerobic Conditions: Efficient Synthesis of Indolizines.

Project description:The Cu(I)-catalyzed denitrogenative transannulation reaction of pyridotriazoles with terminal alkynes en route to indolizines was developed. Compared to the previously reported Rh-catalyzed transannulation reaction, this Cu-catalyzed method features aerobic conditions and much broader scope of pyridotriazoles and alkynes.

| S-EPMC4332698 | biostudies-literature

Asymmetric allylboration of acyl imines catalyzed by chiral diols.

Project description:Chiral BINOL-derived diols catalyze the enantioselective asymmetric allylboration of acyl imines. The reaction requires 15 mol % (S)-3,3'-Ph2-BINOL as the catalyst and allyldiisopropoxyborane as the nucleophile. The reaction products are obtained in good yields (75-94%) and high enantiomeric ratios (95:5-99.5:0.5) for aromatic and aliphatic imines. High diastereoselectivities (diastereomeric ratio > 98:2) and enantioselectivities (enantiomeric ratio > 98:2) are obtained in the reactions of acyl imines with crotyldiisopropoxyboranes. This asymmetric transformation is directly applied to the synthesis of Maraviroc, the selective CCR5 antagonist with potent activity against HIV-1 infection. Mechanistic investigations of the allylboration reaction including IR, NMR, and mass spectrometry studies indicate that acyclic boronates are activated by chiral diols via exchange of one of the boronate alkoxy groups with activation of the acyl imine via hydrogen bonding.

| S-EPMC2638762 | biostudies-literature

Hydroamination of Aromatic Alkynes to Imines Catalyzed by Pd(II)-Anthraphos Complexes.

Project description:Herein, we report the synthesis, characterization, and catalytic performance of cationic Pd(II)-Anthraphos complexes in the intermolecular hydroamination of aromatic alkynes with aromatic amines. The reaction proceeds with 0.18 mol % of catalyst loading, at 90 °C for 4 h under neat conditions. Good to excellent yields could be obtained for a broad range of amines and alkynes.

| S-EPMC7178791 | biostudies-literature

Silver(I) triflate-catalyzed direct synthesis of N-PMP protected alpha-aminopropargylphosphonates from terminal alkynes.

Project description:[reaction: see text] N-PMP protected alpha-aminopropargylphosphonates have been synthesized by using a silver(I) triflate-catalyzed one-pot three-component reaction of terminal alkynes, p-anisidine, and diethyl formylphosphonate hydrate. Good to excellent yields of the desired products may be obtained with a very simple procedure.

| S-EPMC2596881 | biostudies-literature

Palladium-catalyzed asymmetric [3+2] cycloaddition of trimethylenemethane with imines.

Project description: Not available

| S-EPMC2532588 | biostudies-literature

Gold-Catalyzed Regioselective Dimerization of Aliphatic Terminal Alkynes.

Project description:A gold-catalyzed regioselective homodimerization of aliphatic terminal alkynes is described. Bulky and less Lewis acidic tBuXPhosAuNTf(2) is the preferred catalyst, and the additive, anhydrous NaOAc, substantially facilitates the reaction.

| S-EPMC3419542 | biostudies-literature

Enantioselective addition of boronates to acyl imines catalyzed by chiral biphenols.

Project description:On the big screen: A chiral biphenol catalyst screening protocol was developed for the rapid identification of enantioselective nucleophilic boronate reactions with acyl imines (see scheme). The approach successfully identified a unique catalyst for the reaction of aryl, vinyl, and alkynyl boronates. Mechanistic studies demonstrate boronate ligand exchange with the catalyst is necessary for activation towards nucleophilic addition.

| S-EPMC2819183 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

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