Browse
Submit Data
Databases
API
Help

Dataset Information

26 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Enantioselective vinylogous-Mukaiyama-type dearomatisation by anion-binding catalysis.

ABSTRACT: The first enantioselective vinylogous Mukaiyama-type dearomatisation of heteroarenes under anion-binding catalysis is presented. A recyclable tetrakistriazole catalyst was used for the enantiocontrol of the remote vinylogous active position of silyl dienol ethers. This approach provided chiral heterocycles bearing α,β-unsaturated chains with complete regioselectivity and excellent enantioselectivities (up to 97.5 : 2.5 e.r.).

SUBMITTER: Kaur K

PROVIDER: S-EPMC8438702 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Hydrogen bond catalyzed enantioselective vinylogous Mukaiyama aldol reaction.

Project description:[chemical reaction: see text]. The concept of hydrogen bonding catalysis was extended to the vinylogous Mukaiyama aldol reaction, which gives rapid access to polyketide derivatives. The reaction of the silyldienol ether shown and a range of aldehydes catalyzed by TADDOL proceeds regiospecifically to produce the addition products in good yields and enantiomeric excesses.

| S-EPMC2537470 | biostudies-literature

Silanediol Anion Binding and Enantioselective Catalysis.

Project description:Silanediols possess unique and complementary catalytic activity in reactions that are likely to proceed through anion binding. This article directly compares silanediols, thioureas, and squaramides in three separate anion-binding processes. The catalytic abilities of select members of each family are directly correlated to association constant.

| S-EPMC6548508 | biostudies-literature

Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis.

Project description:A highly enantioselective acylation of silyl ketene acetals with acyl fluorides has been developed to generate useful ?,?-disubstituted butyrolactone products. This transformation is promoted by a new thiourea catalyst and 4-pyrrolidinopyridine and represents the first example of enantioselective thiourea anion-binding catalysis with fluoride.

| S-EPMC3164931 | biostudies-literature

A catalytic asymmetric vinylogous Mukaiyama aldol reaction.

Project description:A vinylogous Mukaiyama aldol reaction, conducted using 10 mol % of a BITIP catalyst and B(OMe)3 as an additive, effects an enantioselective four-carbon chain extension to give versatile E-alpha,beta-unsaturated thiol esters.

| S-EPMC2516376 | biostudies-literature

Enantioselective dearomatization of isoquinolines by anion-binding catalysis en route to cyclic ?-aminophosphonates.

Project description:An enantioselective dearomatization of isoquinolines has been developed using chiral anion-binding catalysis. This transformation, catalyzed by a simple and easy to prepare tert-leucine-based thiourea derivative, makes use of silyl phosphite as a nucleophile and generates cyclic ?-aminophosphonates. This is the first time asymmetric anion-binding catalysis has been applied to the synthesis of ?-aminophosphonates.

| S-EPMC5465551 | biostudies-literature

Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of ?-Amino Esters.

Project description:The enantioselective oxidative C-H functionalization of tetrahydroisoquinoline derivatives is achieved through the merger of photoredox and asymmetric anion-binding catalysis. This combination of two distinct catalysis concepts introduces a potentially general approach to asymmetric transformations in oxidative photocatalysis.

| S-EPMC3842187 | biostudies-literature

Stereodivergent Anion Binding Catalysis with Molecular Motors.

Project description:A photoresponsive chiral catalyst based on an oligotriazole-functionalized unidirectional molecular motor has been developed for stereodivergent anion binding catalysis. The motor function controls the helical chirality of supramolecular assemblies with chloride anions, which by means of chirality transfer enables the enantioselective addition of a silyl ketene acetal nucleophile to oxocarbenium cations. Reversal of stereoselectivity (up to 142?% ?ee) was achieved through rotation of the motor core induced by photochemical and thermal isomerization steps.

| S-EPMC7004205 | biostudies-literature

Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis.

Project description:BackgroundThe diastereoselectivity of a vinylogous Mukaiyama aldol reaction of a series of N-substituted 4-oxy-2-trimethylsilyloxypyrroles with a tartrate-based aldehyde has been explored as a model reaction for castanospermine synthesis.ResultsThe study has revealed that the reaction is sensitive to the nature of the combination of N- and 4-oxy substituents. With a N-PMB or N-Bn and 4-methoxy combination, the reaction generates an aldol adduct with the correct absolute configurations for C-8 and C-8a of the indolizidine alkaloid castanospermine. The adduct was transformed to an indolizidine, whose ketal could not be transformed appropriately for the target alkaloid.ConclusionThe first successful diastereoselective Mukaiyama aldol strategy for the C-8 and C-8a stereogenic centres of castanospermine is presented using silyloxypyrrole chemistry. The results suggest that a full enantioselective synthesis can be realized provided that C-1 functionalisation is accomplished early in the synthesis, post-coupling.

| S-EPMC2151077 | biostudies-literature

Enantioselective 1,1-arylborylation of alkenes: merging chiral anion phase transfer with Pd catalysis.

Project description:A palladium-catalyzed three-component coupling of α-olefins, aryldiazonium salts, and bis(pinacolato)diboron affords direct access to chiral benzylic boronic esters. This process is rendered highly enantioselective using an unprecedented example of cooperative chiral anion phase transfer and transition-metal catalysis.

| S-EPMC4564013 | biostudies-literature

On- and Off-Cycle Catalyst Cooperativity in Anion-Binding Catalysis.

Project description:Chiral, neutral H-bond donors have found widespread use as catalysts in enantioselective reactions involving ion-pair intermediates. Herein, a systematic mechanistic study of a prototypical anion-binding reaction, the thiourea-catalyzed enantioselective alkylation of ?-chloroethers, is detailed. This study reveals that the catalyst resting state is an inactive dimeric aggregate that must dissociate and then reassemble to form a 2:1 catalyst-substrate complex in the rate-determining transition structure. Insight into this mode of catalyst cooperativity sheds light on the practical limitations that have plagued many of the H-bond donor-catalyzed reactions developed to date and suggests design strategies for new, highly efficient catalyst structures.

| S-EPMC5108296 | 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