Browse
Submit Data
Databases
API
Help

Dataset Information

25 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Organocatalytic Fluorogenic Synthesis of Chromenes.

ABSTRACT: Two fluorescent derivatives of 2-amino-3-carbonitrile-4H-chromene were synthesized by means of a fluorogenic Michael addition of dimedone to dicyano alkene labeled BODIPY derivatives. Different organocatalysts were used in different conditions to obtain compounds 3 and 4 in good yield (up to 65% and 85%) and moderate enantiomeric excess (51% and 41% ee, respectively). This work provides the first example of an enantioselective organocatalytic conversion combined with fluorogenesis.

SUBMITTER: Raeisolsadati Oskouei M

PROVIDER: S-EPMC5393152 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Organocatalytic Fluorogenic Synthesis of Chromenes.

Raeisolsadati Oskouei Mina M Brouwer Albert M AM

Journal of fluorescence 20170221 3

Two fluorescent derivatives of 2-amino-3-carbonitrile-4H-chromene were synthesized by means of a fluorogenic Michael addition of dimedone to dicyano alkene labeled BODIPY derivatives. Different organocatalysts were used in different conditions to obtain compounds 3 and 4 in good yield (up to 65% and 85%) and moderate enantiomeric excess (51% and 41% ee, respectively). This work provides the first example of an enantioselective organocatalytic conversion combined with fluorogenesis. ...[more]

PMID: 28224357

Similar Datasets

Catalytic enantioselective synthesis of 2-aryl-chromenes.

Project description:An enantioselective Pd-catalyzed 6-endo-trig reaction for the synthesis of 2-aryl-chromenes has been developed. A systematic optimization of a TADDOL-derived ligand set resulted in the identification of a novel monodentate phosphoramidite-palladium catalyst that accesses 2-aryl-2H-chromenes with high yield and enantioselectivity under mild conditions. The products obtained from this method can be transformed into biologically active compounds through functionalization of the chromene alkene.

| S-EPMC4334165 | biostudies-literature

Enantioselective organocatalytic Hantzsch synthesis of polyhydroquinolines.

Project description:The four-component Hantzsch reaction provides access to pharmaceutically important dihydropyridines. To expand the utility of this method, we have developed a route under organocatalytic conditions with good yields and excellent ee's. Through catalyst screening, we found that a BINOL-phosphoric acid allowed enantioselective synthesis of six-membered heterocycles with a variety of substitution patterns.

| S-EPMC2727599 | biostudies-literature

Organocatalytic Enantiospecific Total Synthesis of Butenolides.

Project description:Biologically important, chiral natural products of butenolides, (-)-blastmycinolactol, (+)-blastmycinone, (-)-NFX-2, (+)-antimycinone, lipid metabolites, (+)-ancepsenolide, (+)-homoancepsenolide, mosquito larvicidal butenolide and their analogues were synthesized in very good yields in a sequential one-pot manner by using an organocatalytic reductive coupling and palladium-mediated reductive deoxygenation or organocatalytic reductive coupling and silica-mediated reductive deamination as the key steps.

| S-EPMC8306825 | biostudies-literature

Organocatalytic enantioselective synthesis of alpha-hydroxy phosphonates.

Project description:Tertiary alpha-hydroxy phosphonates have been synthesized in good yields and high enantiomeric purity (up to 99% ee) through a novel l-proline-catalyzed cross aldol reaction of alpha-keto phosphonates and ketones.

| S-EPMC2535926 | biostudies-literature

Organocatalytic Synthesis of Methylene-Bridged N-Heterobiaryls.

Project description:A one-step synthesis of 1,1'- and 2,2'-methylene-bridged N-heterobiaryls directly from the corresponding N-heterocycles in a reaction with methylmagnesium chloride in the presence of catalytic amounts of N,N,N',N'-tetramethylethylenediamine under thermal and microwave conditions is reported. The split-and-merge methylenation of 2,2'-N-heterobiaryls and the direct ortho-alkylation of quinoline and isoquinoline with Grignard reagents have also been developed. Mechanistic studies identified several intermediates and provided insight into the formation and roles of magnesium hydride species in the process.

| S-EPMC5148643 | biostudies-literature

Organocatalytic asymmetric synthesis of Si-stereogenic silacycles.

Project description:A strong and confined Brønsted acid catalyzed enantioselective cyclization of bis(methallyl)silanes provides enantioenriched Si-stereogenic silacycles. High enantioselectivities of up to 96.5:3.5 er were obtained for a range of bis(methallyl)silanes. NMR and ESI-MS studies reveal that the formation of a covalent adduct irreversibly inhibits turnover. Remarkably, we found that acetic acid as an additive promotes the collapse of this adduct, enabling full turnover. Experimental investigation and density functional theory (DFT) calculations were conducted to elucidate the origin of this phenomenon and the observed enantioselectivity.

| S-EPMC11239892 | biostudies-literature

Organocatalytic atroposelective synthesis of axially chiral styrenes.

Project description:Axially chiral compounds are widespread in biologically active compounds and are useful chiral ligands or organocatalysts in asymmetric catalysis. It is well-known that styrenes are one of the most abundant and principal feedstocks and thus represent excellent prospective building blocks for chemical synthesis. Driven by the development of atroposelective synthesis of axially chiral styrene derivatives, we discovered herein the asymmetric organocatalytic approach via direct Michael addition reaction of substituted diones/ketone esters/malononitrile to alkynals. The axially chiral styrene compounds were produced with good chemical yields, enantioselectivities and almost complete E/Z-selectivities through a secondary amine-catalysed iminium activation strategy under mild conditions. Such structural motifs are important precursors for further transformations into biologically active compounds and synthetic useful intermediates and may have potential applications in asymmetric synthesis as olefin ligands or organocatalysts.

| S-EPMC5418600 | biostudies-literature

Organocatalytic highly enantioselective synthesis of secondary alpha-hydroxyphosphonates.

Project description:[reaction: see text] The first organocatalytic cross aldol reaction of ketones and diethyl formylphosphonate hydrate has been realized by using readily available l-prolinamide as the catalyst. Secondary alpha-hydroxyphosphonates have been synthesized in high enantioselective (up to >99% ee) and good diastereoselectivity.

| S-EPMC2525621 | biostudies-literature

Organocatalytic Stereoselective Synthesis of Fluorinated 3,3'-Linked Bisoxindoles.

Project description:A highly diastereoselective organocatalytic method that produces 3-fluoro-3'-hydroxy-3,3'-bisoxindoles and the corresponding 3-fluoro-3'-amino derivatives having two adjacent chirality centers from fluorooxindoles and isatins in high yields is described. The reaction occurs in protic solvents at room temperature, it can be upscaled without compromising yield and stereoselectivity, and chromatographic product purification is not required.

| S-EPMC5939997 | biostudies-literature

Erratum: Organocatalytic atroposelective synthesis of axially chiral styrenes.

Project description:This corrects the article DOI: 10.1038/ncomms15238.

| S-EPMC5490258 | biostudies-literature