Intramolecular Pauson Research Articles

ChemInform Abstract: Scope and Limitation of Intramolecular Pauson—Khand Reaction of Fluorine‐Containing Enynes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A Short Synthesis of (±)-13-Deoxyserratine

A short and efficient total synthesis of (±)-13-deoxyserratine (3) features a highly stereoselective intramolecular Pauson–Khand reaction of 1 and a cascade of radical cyclizations starting with the amidyl radical 2. The desired alkaloid 3 was thus obtained in ten steps in an overall yield of 12 %. THP=tetrahydropyranyl, TBS=tert-butyldimethylsilyl.

Synthesis of enantiopure 3-azabicyclo[3.3.0]octen-7-one derivatives via intramolecular Pauson-Khand cycloaddition reaction using tri-O-acetyl-D-glucal as starting material.

Some N-substituted-3-azabicyclo[3.3.0]octen-7-one derivatives have been synthesized in an enantiomerically pure form starting from tri-O-acetyl-D-glucal via intramolecular Pauson-Khand (IPK) cycloaddition.

ChemInform Abstract: Annulation of 3‐Methylcyclopentenone onto a Cyclopentenol Double Bond by Intramolecular Pauson—Khand Reaction.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Monocyclopentadienyltitanium Aryloxide Complexes: Preparation, Characterization, and Application in Cyclization Reactions

A variety of monocyclopentadienyltitanium aryloxide complexes were prepared, characterized by X-ray crystallography, and used to catalyze or mediate cyclization reactions. Structural characterization allowed for the comparison of steric parameters of various 2,6-disubstituted aryloxide ligands. Transformations of dienes and enynesincluding the catalysis of a 1,6-diene cycloisomerization and the intramolecular Pauson−Khand reactionwere investigated. A titanium metallacycle was prepared from a sterically hindered enyne containing a trisubstituted olefin. The Pauson−Khand reaction of trimethylsilyl-substituted enynes was promoted to generate α-silylcyclopentenones.

An intramolecular Pauson–Khand approach to the synthesis of chiral cyclopentadienes

A procedure for the synthesis of chirally-substituted cyclopentadienes has been developed by employing the intramolecular Pauson–Khand reaction of chiral amides derived from 8-nonen-2-ynoic acid. Hydride-mediated reduction of the resulting cyclopentenone adducts followed by acid-catalysed dehydration leads to the formation of the corresponding cyclopentadienes in good overall yield.

Dendritic effect in polymer-supported catalysis of the intramolecular Pauson-Khand reaction.

A remarkable increase in catalytic activity and selectivity in the intramolecular Pauson-Khand reaction is observed for Co complexes, immobilised on second- and third-generation dendron-functionalized polystyrene, as compared with their analogues on non-dendronized support.

Selective transformations of differently functionalized 4-ethynyl-octa-1,7-dienes and 5-ethynyl-nona-1,8-dienes via intramolecular Pauson–Khand reaction: preparation of new and useful building blocks for the synthesis of angularly fused triquinanes

The intramolecular Pauson–Khand (PK) reaction of 4-bromomethyldimethylsilyloxy-4-ethynyl-6,6-dimethyloct-1-en-7-yne ( 1 ), the differently functionalized 4-ethynyl-octa-1,7-dienes ( 2– 6 ), and 5-ethynyl-5-hydroxy-2,4,4-trimethyl-nona-1,8-diene ( 7 ) is reported. The resulting bicyclo[3.3.0]oct-1-en-3-ones ( 22– 29 ) and ( 33– 35 ) have been obtained in good yield, with moderate stereoselectivity. Major isomers ( 22 , 24 , 26 , 28 ) have the free or protected hydroxyl group cis to H-6a at the fused ring carbon. In dienyne compound 7 the gem-dimethyl functional group, with the same length for both alkenyl chains, dictates the regiochemistry of the PK reaction, affording major bicyclo derivatives 33 and 34 (in a 4.6:1 ratio, the major isomer ( 33 ) having the free hydroxyl group cis to the methyl group at C-6a), and compound 35 with the hydroxyl group trans to proton H-6a at ring junction. All new adducts are potential useful building blocks for the total synthesis of angularly fused triquinanes.

ChemInform Abstract: Synthesis of Bridged Medium‐Sized Rings Through the Intramolecular Pauson—Khand Reaction.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Seven membered rings via intramolecular Pauson–Khand reactionsElectronic supplementary data (ESI) available: spectroscopic and analytical characterization of compounds 5–8 and 10. See http://www.rsc.org/suppdata/cc/b1/b108134a/

Seven membered rings are obtained with good yields by intramolecular Pauson–Khand reactions of some aromatic compounds.

ChemInform Abstract: Synthetic Studies on Lycopodium Alkaloid, Magellanine: Stereoselective Construction of Functionalized Angular Tricyclic Skeletons by Intramolecular Pauson—Khand Reaction.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Scope and limitation of intramolecular Pauson–Khand reaction of fluorine-containing enynes

Intramolecular Pauson–Khand reaction of various fluorine-containing enynes was investigated under various conditions. The reaction of the substrates, which have fluorine atom(s) or fluorine-containing group(s) attached to alkenyl moiety, gave the corresponding cyclopentenones in low to moderate yield, while that of the substrates bearing fluorine-containing groups attached to alkynyl moiety afforded the corresponding cyclopentenones in low to high yield.

ChemInform Abstract: Investigation of the Synthesis of Angular Tricyclic Compounds by Intramolecular Pauson—Khand Reaction of exo‐ and endo‐Cyclic Enynes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Synthesis of bridged medium-sized rings through the intramolecular Pauson-Khand reaction.

[reaction: see text] A series of aromatic enynes containing steric buttressing elements were prepared and evaluated in the NMO-mediated Pauson-Khand cyclization. O-Allyl systems led to the expected angularly fused products, whereas the O-butenyl and O-pentenyl derivatives afforded the unprecedented bridge systems.

Synthetic Studies on Lycopodium Alkaloid, Magellanine: Stereoselective Construction of Functionallized Angular Tricyclic Skeletons by Intramolecular Pauson–Khand Reaction

Abstract Angular tricyclic compounds as intermediates for total synthesis of magellanine were synthesized by stereoselective Ireland–Claisen rearrangement and intramolecular Pauson–Khand reaction of exo-methylenecyclohexylalkynes. Interestingly, remarkably different reactivity was observed in the Pauson–Khand reaction of cis- and trans-disubstituted exo-methylenecyclohexylalkynes.

Annulation of 3-methylcyclopentenone onto a cyclopentenol double bond by intramolecular Pauson–Khand reaction

A procedure for regio- and diastereocontrolled annulation of a 3-methylcyclopentenone moiety on a cyclopentenol double bond has been developed by employing the Pauson–Khand reaction in the presence of a promoter having reductive potential. During the examination, a novel substrate specific 3-hydroxycyclopentanone formation reaction was also discovered.

ChemInform Abstract: Synthesis of Medium‐Sized Rings Using the Intramolecular Pauson—Khand Reaction.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Diastereoselective Pauson–Khand reactions on aromatic substrates

The synthesis of several natural products’ frameworks is carried out by means of a diastereoselective intramolecular Pauson–Khand reaction promoted by molecular sieves. Diastereoselectivity is achieved only if a coordinating group is present at a convenient distance from the alkene moiety. Naphthalenes can be obtained directly under refluxing toluene conditions.

Investigation of the synthesis of angular tricyclic compounds by intramolecular Pauson–Khand reaction of exo- and endo-cyclic enynes

Intramolecular Pauson–Khand reaction of various alkynyl exo-alkylidene-cyclohexanes and -pentane gives angular type 6–5–5 and 5–5–5 tricyclic compounds in good to high yield. The present reaction also offers convenient construction of two contiguous quaternary centers, which could not be synthesized from alkynyl endo-cycloolefins. Scope and limitation of the present reaction of various exo- and endo-cyclic enynes are also described.

Synthesis of medium-sized rings using the intramolecular Pauson–Khand reaction

The dicobalthexacarbonyl alkyne complex of a series of enynes templated on aromatic rings has been shown to undergo the Pauson–Khand reaction to generate medium-sized rings.