Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of cross-conjugated trienes by rhodium-catalyzed dimerization of monosubstituted allenes.

ABSTRACT: A rhodium(I)/dppe catalyst promoted dimerization of monosubstituted allenes in a stereoselective manner to give cross-conjugated trienes, which are different from those obtained by a palladium catalyst.

SUBMITTER: Miura T

PROVIDER: S-EPMC3107559 | biostudies-literature | 2011

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis of cross-conjugated trienes by rhodium-catalyzed dimerization of monosubstituted allenes.

Miura Tomoya T Biyajima Tsuneaki T Toyoshima Takeharu T Murakami Masahiro M

Beilstein journal of organic chemistry 20110509

A rhodium(I)/dppe catalyst promoted dimerization of monosubstituted allenes in a stereoselective manner to give cross-conjugated trienes, which are different from those obtained by a palladium catalyst. ...[more]

PMID: 21647266

Similar Datasets

NHC-Cu-catalyzed protoboration of monosubstituted allenes. Ligand-controlled site selectivity, application to synthesis and mechanism.

Project description:Two types of NHC-Cu complexes catalyze protoborations of terminal allenes to afford valuable 1,1- or trisubstituted vinylboron species with high site selectivity and stereoselectivity. The scope of the method, application to natural product synthesis, and mechanistic basis for the observed selectivity trends are presented.

| S-EPMC3625862 | biostudies-literature

Platinum(II)-catalyzed intermolecular hydroamination of monosubstituted allenes with secondary alkylamines.

Project description:A 1:1 mixture of (dppf)PtCl(2) and AgOTf (5 mol%) catalyzed the intermolecular hydroamination of monosubstituted allenes with secondary alkylamines at 80 degrees C to form allylic amines in good yield with selective formation of the E-diastereomer.

| S-EPMC2924659 | biostudies-literature

Synthesis of Cross-Conjugated Polyenes via Palladium-Catalyzed Oxidative C-C Bond Forming Cascade Reactions of Allenes.

Project description:An efficient palladium-catalyzed oxidative C-C bond forming cascade reaction of allenes involving a coupling between an enallene and an allenyne followed by a carbocyclization of the generated Pd-intermediate was developed. This cascade reaction afforded functionalized cross-conjugated polyenes. The enallene is initially activated by palladium and reacts with the allenyne to give the cross-conjugated polyenes.

| S-EPMC7311062 | biostudies-literature

Rhodium-catalyzed chemo- and regioselective cross-dimerization of two terminal alkynes.

Project description:Cross-dimerization of terminal arylacetylenes and terminal propargylic alcohols/amides has been achieved in the presence of a rhodium catalyst. This method features high chemo- and regioselectivities rendering convenient and atom economical access to functionalized enynes.

| S-EPMC3697770 | biostudies-literature

Allene-alkyne cross-coupling for stereoselective synthesis of substituted 1,4-dienes and cross-conjugated trienes.

Project description:Titanium-mediated cross-coupling of allenic alcohols with alkynes has been investigated. Divergent reaction pathways were discovered that provide either stereodefined 1,4-dienes or substituted cross-conjugated trienes. In short, allene substitution plays a critical role in the determination of reaction pathway.

| S-EPMC2577592 | biostudies-literature

Rhodium-catalyzed asymmetric intramolecular hydroarylation of allenes: access to functionalized benzocycles.

Project description:A rhodium-catalyzed regio- and enantioselective cyclization of tethered allenylbenzenes is reported. Employing a RhI/Josiphos catalytic system a diverse set of 6-membered, ?-chiral benzocycles were obtained, scaffolds found in many bioactive compounds. Moreover, a gram scale reaction as well as the application of suitable transformations are demonstrated.

| S-EPMC6977554 | biostudies-literature

Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.

Project description:In this study, we establish that conjugated enynes undergo selective 1,4-hydroamination under Pd catalysis to deliver chiral allenes with pendant allylic amines. Several primary and secondary aliphatic and aryl-substituted amines couple with a wide range of mono- and disubstituted enynes in a nonenantioselective reaction where DPEphos serves as the ligand for Pd. Benzophenone imine acts as an ammonia surrogate to afford primary amines in a two-step/one-pot process. Examination of chiral catalysts revealed a high degree of reversibility in the C-N bond formation that negatively impacted enantioselectivity. Consequently, an electron-poor ferrocenyl-PHOX ligand was developed to enable efficient and enantioselective enyne hydroamination.

| S-EPMC6568270 | biostudies-literature

Iron-catalyzed Cross-Coupling of Propargyl Carboxylates and Grignard Reagents: Synthesis of Substituted Allenes.

Project description:Presented herein is a mild, facile, and efficient iron-catalyzed synthesis of substituted allenes from propargyl carboxylates and Grignard reagents. Only 1-5 mol % of the inexpensive and environmentally benign [Fe(acac)3 ] at -20 °C was sufficient to afford a broad range of substituted allenes in excellent yields. The method tolerates a variety of functional groups.

| S-EPMC4797716 | biostudies-literature

Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes.

Project description:Benzofused seven-membered heterocycles such as 1,4-benzo[e]diazepines (1,4-BZDs) and 1,4-benzo[e]oxazepines (1,4-BZOs) were efficiently synthesized by Rh-catalyzed hydrofunctionalization of internal alkynes and allenes in good to excellent yields. The asymmetric hydroamination of (aminomethyl)anilines gave rise to 3-vinyl-1,4-BZDs with excellent enantioselectivities. Orthogonal N-deprotection of 1,4-BZDs allowed an easy entry to an advanced pyrrolobenzodiazepine metabolite of the V2-receptor antagonist Lixivaptan.

| S-EPMC8499028 | biostudies-literature

Iron-Catalyzed Cross-Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols.

Project description:Herein we disclose an iron-catalyzed cross-coupling reaction of propargyl ethers with Grignard reagents. The reaction was demonstrated to be stereospecific and allows for a facile preparation of optically active allenes via efficient chirality transfer. Various tri- and tetrasubstituted fluoroalkyl allenes can be obtained in good to excellent yields. In addition, an iron-catalyzed cross-coupling of Grignard reagents with α-alkynyl oxetanes and tetrahydrofurans is disclosed herein, which constitutes a straightforward approach towards fully substituted β- or γ-allenols, respectively.

| S-EPMC8518087 | 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