Browse
Submit Data
Databases
API
Help

Dataset Information

25 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis.

ABSTRACT: We report herein an efficient synthesis of furopyran derivatives through a gold(I)-catalyzed domino reaction. The cascade reaction starts with two regioselective cyclizations, a 5-endo-dig and a 8-endo-dig, followed with a Grob-type fragmentation and a hetero Diels-Alder. The obtained furopyran derivatives contain fused and spiro-heterocycles. During this one-pot process, four bonds and four controlled stereogenic centers including a quaternary center are formed.

SUBMITTER: Ruch M

PROVIDER: S-EPMC7663467 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis.

Ruch Marie M Brach Nicolas N Galéa Roméric R Wagner Patrick P Blond Gaëlle G

Molecules (Basel, Switzerland) 20201027 21

We report herein an efficient synthesis of furopyran derivatives through a gold(I)-catalyzed domino reaction. The cascade reaction starts with two regioselective cyclizations, a 5-<i>endo</i>-dig and a 8-<i>endo</i>-dig, followed with a Grob-type fragmentation and a hetero Diels-Alder. The obtained furopyran derivatives contain fused and spiro-heterocycles. During this one-pot process, four bonds and four controlled stereogenic centers including a quaternary center are formed. ...[more]

PMID: 33121149

Similar Datasets

Gold(I)-catalyzed domino cyclization for the synthesis of polyaromatic heterocycles.

Project description:Gold(I) complexes have emerged as powerful and useful catalysts for the formation of new C-C, C-O and C-N bonds. Taking advantage of the specificity of [IPrAuNCMe][SbF6] complexes to favor the 5-exo-dig cyclization over the 6-endo-dig pathway, we report a high yielding and efficient method to generate substituted polyaromatic heterocycles under remarkably mild reaction conditions.

| S-EPMC3869369 | biostudies-literature

Synthesis of indolines via a domino Cu-catalyzed amidation/cyclization reaction.

Project description:A highly efficient one-pot procedure for the synthesis of indolines and their homologues based on a domino Cu-catalyzed amidation/nucleophilic substitution reaction has been developed. Substituted 2-iodophenethyl mesylates and related compounds afforded the corresponding products in excellent yields. No erosion of optical purity was observed when transforming enantiomerically pure mesylates under the reaction conditions.

| S-EPMC2489202 | biostudies-literature

Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines.

Project description:An Ugi four-component reaction of propargylamine with 3-formylindole and various acids and isonitriles produces adducts which are subjected to a cationic gold-catalyzed diastereoselective domino cyclization to furnish diversely substituted spiroindolines. All the reactions run via an exo-dig attack in the hydroarylation step followed by an intramolecular diastereoselective trapping of the imminium ion. The whole sequence is atom economic and the application of a multicomponent reaction assures diversity.

| S-EPMC3817510 | biostudies-literature

Stereoselective synthesis of chromane derivatives via a domino reaction catalyzed by modularly designed organocatalysts.

Project description:A highly enantio- and diastereoselective method for the synthesis of functionalized chroman-2-ones and chromanes was achieved by using an organocatalytic domino Michael/hemiacetalization reaction of aliphatic aldehydes and (E)-2-(2-nitrovinyl)phenols followed by a PCC oxidation and dehydroxylation, respectively. Using the modularly designed organocatalysts (MDOs) self-assembled from cinchona alkaloid derivatives and amino acids in the reaction media, the title products were obtained in good to high yields (up to 97%) and excellent diastereoselectivities (up to 99?:?1 dr) and enantioselectivities (up to 99% ee).

| S-EPMC6317902 | biostudies-literature

Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction.

Project description:An NHC-catalyzed regio- and stereoselective Mannich/lactamization domino reaction of N-(benzothiazolyl)imines with ?-chloroaldehydes has been developed. This new protocol provides a facile approach for the asymmetric synthesis of benzothiazolo-pyrimidinones and a pyrrolo[1,2-a]indolone in moderate to good yields (34-78%) and excellent stereoselectivities (87-99% ee, up to >20?:?1 d.r.).

| S-EPMC4612130 | biostudies-literature

Ru-NHC Catalyzed Domino Reaction of Carbonyl Compounds and Alcohols: A Short Synthesis of Donaxaridine.

Project description:Direct α-alkylation of amides and the synthesis of C3-alkylated 3-hydroxyindolin-2-one/2-substituted-2-hydroxy-3,4-dihydronaphthalen-1(2H)-one derivatives from 2-oxindole/1-teralone were reported using primary alcohols in the presence of Ru-NHC catalyst in a one pot condition under the borrowing hydrogen method. In the case of inert conditions, 2-oxindole/1-teralone exclusively forms the C3-alkylated product. Whereas, allowing this reaction mixture to occur under an air atmosphere predominantly forms C3-alkylated 3-hydroxyindolin-2-one via domino C-H alkylation and aerobic C-H hydroxylation. This Ru-NHC catalyst is easily accessible, air stable, and phosphine free. Using this method, synthesis of 2-oxindole based natural products such as Donaxaridine was accomplished.

| S-EPMC6645123 | biostudies-literature

A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction.

Project description:Herein we report a novel palladium-catalyzed reaction that results in phenanthrene derivatives using aryl iodides, ortho-bromobenzoyl chlorides and norbornadiene in one pot. This dramatic transformation undergoes ortho-C-H activation, decarbonylation and subsequent a retro-Diels-Alder process. Pleasantly, this protocol has a wider substrate range, shorter reaction times and higher yields of products than previously reported methods.

| S-EPMC6369988 | biostudies-literature

Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction.

Project description:An NHC-catalyzed Michael/Michael/esterification domino reaction via homoenolate/enolate intermediates for the asymmetric synthesis of tetrasubstituted cyclopentanes bearing four contiguous stereocenters is described. A variety of α,β-unsaturated aldehydes and 2-nitroallylic acetates react well with good domino yields and high stereoselectivities.

| S-EPMC5315016 | biostudies-literature

Stereoselective Synthesis of 3-Oxabicyclo[3.3.1]nonan-2-ones via a Domino Reaction Catalyzed by Modularly Designed Organocatalysts.

Project description:A highly stereoselective method for the synthesis of functionalized 3-oxabicyclo[3.3.1]nonan-2-one derivatives with four contiguous stereogenic centers, including one tetrasubstituted stereogenic center, was realized through an organocatalytic domino Michael-hemiacetalization-Michael reaction of (E)-3-aryl-2-nitroprop-2-enols and (E)-7-aryl-7-oxohept-5-enals followed by a PCC oxidation. Using the modularly designed organocatalysts (MDOs) self-assembled from cinchona alkaloid derivatives and amino acids in the reaction media, the title products were obtained in good yields (up to 84%), excellent diastereoselectivities (> 99:1 dr), and high enantioselectivities (up to 96% ee).

| S-EPMC6715131 | biostudies-literature

Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles.

Project description:A microwave-assisted three-component protocol involving N-1 alkylation of 2-alkynylindoles with epichlorohydrin, ring opening of the epoxide with sodium azide, and an intramolecular Huisgen azide-internal alkyne 1,3-dipolar cycloaddition domino sequence has been described. The efficacy of the methodology has been demonstrated by treating various 2-alkynylindoles (aromatic/aliphatic) with epichlorohydrin and sodium azide furnishing annulated tetracyclic indolodiazepinotriazoles in satisfactory yields.

| S-EPMC3596043 | biostudies-other

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