Browse
Submit Data
Databases
API
Help

Dataset Information

31 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Torquoselective ring closures of chiral amido trienes derived from allenamides. A tandem allene isomerization-pericyclic ring-closure-intramolecular Diels-Alder cycloaddition.

ABSTRACT: A new torquoselective ring-closure of chiral amide-substituted 1,3,5-hexatrienes and its application in tandem with [4 + 2] cycloaddition are described. The trienes were derived via either a 1,3-H or 1,3-H-1,7-H shift of alpha-substituted allenamides, and the entire sequence through the [4 + 2] cycloaddition could be in tandem from allenamides.

SUBMITTER: Hayashi R

PROVIDER: S-EPMC2862010 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Torquoselective ring closures of chiral amido trienes derived from allenamides. A tandem allene isomerization-pericyclic ring-closure-intramolecular Diels-Alder cycloaddition.

Hayashi Ryuji R Feltenberger John B JB Hsung Richard P RP

Organic letters 20100301 6

A new torquoselective ring-closure of chiral amide-substituted 1,3,5-hexatrienes and its application in tandem with [4 + 2] cycloaddition are described. The trienes were derived via either a 1,3-H or 1,3-H-1,7-H shift of alpha-substituted allenamides, and the entire sequence through the [4 + 2] cycloaddition could be in tandem from allenamides. ...[more]

PMID: 20170149

Similar Datasets

Regio- and stereoselective isomerizations of allenamides: synthesis of 2-amido-dienes and their tandem isomerization-electrocyclic ring-closure.

Project description:A regio- and stereoselective isomerization of allenamides is described, leading to preparations of de novo 2-amido-dienes and a tandem isomerization-6pi-electron electrocyclic ring-closure.

| S-EPMC2732350 | biostudies-literature

Facile Synthesis of 3-Amido-Dienynes via a Tandem ?-Propargylation-Isomerization of Chiral Allenamides and their Applications in Diels-Alder Cycloadditions.

Project description:A series of de novo 3-amido-dienynes was synthesized via tandem ?-propargylation-isomerization of chiral allenamides with moderate E/Z ratio. Reactivities of E-and Z-isomers were examined.

| S-EPMC6000824 | biostudies-literature

An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts.

Project description:Preparations of de novo acyclic 2-amido-dienes and 3-amido-trienes through 1,3-hydrogen shifts from allenamides are described. These 1,3-hydrogen shifts could be achieved thermally or they could be promoted by the use of Brønsted acids. Under either condition, these processes are highly regioselective in favour of the ?-position, and highly stereoselective in favour of the E-configuration. In addition, 6?-electron electrocyclic ring-closure could be carried out with 3-amido-trienes to afford cyclic 2-amido-dienes, and such electrocyclic ring-closure could be rendered in tandem with the 1,3-hydrogen shift.

| S-EPMC3079123 | biostudies-literature

Intramolecular Diels-Alder reactions of siloxacyclopentene constrained trienes.

Project description:The synthesis of siloxacyclopentene-constrained trienes 7 and 10 and studies of their IMDA cycloadditions are described. The use of appropriately chosen thermal or Lewis acid conditions allows for cycloadducts 3-6 to be obtained with high levels of diastereoselectivity. These adducts possess trans-relationships between the hydroxyl group and the adjacent ring fusion proton, a stereochemical relationship not previously attainable in IMDA reactions.

| S-EPMC2504012 | biostudies-literature

Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines.

Project description:Chiral 2-oxazolines are valuable building blocks and famous ligands for asymmetric catalysis. The most common synthesis involves the reaction of an amino alcohol with a carboxylic acid. In this paper, an efficient synthesis of 2-oxazolines has been achieved via the stereospecific isomerization of 3-amido-2-phenyl azetidines. The reactions were studied in the presence of both Brønsted and Lewis acids, and Cu(OTf)2 was found to be the most effective.

| S-EPMC7914936 | biostudies-literature

Oppolzer-type intramolecular Diels-Alder cycloadditions via isomerizations of allenamides.

Project description:A new approach to Oppolzer's intramolecular Diels-Alder cycloaddition (IMDA) through γ-isomerization of readily available N-tethered allenamides is described. These IMDA reactions are carried out in tandem with the allenamide isomerization or 1,3-H shift, leading to complex nitrogen heterocycles in a highly stereoselective manner.

| S-EPMC3112474 | biostudies-literature

Synthesis of amido-spiro[2.2]pentanes via Simmons-Smith cyclopropanation of allenamides.

Project description:A detailed account of Simmons-Smith cyclopropanations of allenamides en route to amido-spiro[2.2]pentanes is described here. While the diastereoselectivity was low when using unsubstituted allenamides, the reaction is overall efficient and general, representing the most direct synthesis of both chemically and biologically interesting amido-spiro[2.2]pentane systems. With alpha-substituted allenamides, while the diastereoselectivity could be improved significantly based on a series of conformational analyses, both mono- and bis-cyclopropanation products were observed. Consequently, several structurally intriguing amido-methylene cyclopropanes could also be prepared.

| S-EPMC2829688 | 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

A tandem 1,3-H-shift-6π-electrocyclization-cyclic 2-amido-diene intramolecular Diels-Alder cycloaddition approach to BCD-Ring of atropurpuran.

Project description:An approach toward the BCD-ring of atropurpuran via a sequence of allenic 1,3-H shift, 6π-electron pericyclic ring closure, and intramolecular Diels-Alder cycloaddition of cyclic 2-amidodiene is described.

| S-EPMC3253247 | biostudies-literature

Thermal intramolecular [4 + 2] cycloadditions of allenamides: a stereoselective tandem propargyl amide isomerization-cycloaddition.

Project description:A stereoselective intramolecular normal demand [4 + 2] cycloaddition of allenamides under thermal conditions without metal assistance is described. This work led to the development of a stereoselective tandem propargyl amide-isomerization-[4 + 2] cycloaddition sequence amenable for rapid assembly of complex nitrogen heterocycles.

| S-EPMC2736324 | 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