Ruthenium-catalyzed Cross-metathesis Research Articles

Grubbs's Cross Metathesis of Eugenol with cis-2-Butene-1,4-diol To Make a Natural Product. An Organometallic Experiment for the Undergraduate Lab

An experiment for the undergraduate organic laboratory course, the ruthenium catalyzed cross metathesis of eugenol with cis-1,4-butenediol, is described in detail. The Grubbs' catalyst is dispersed in paraffin wax to eliminate the need for inert atmosphere storage. Eugenol, the main component of clove oil, is coupled at room temperature overnight with cis-1,4-butenediol to yield the crystalline (E)-4-(4-hydroxy-3-methoxyphenyl)but-2-en-ol, also a natural product. The experiment is an excellent example of the powerful selectivity possible with the Grubbs' catalyst. Both the preference for trans over cis alkene formation and for cross metathesis over homodimerization are demonstrated. The experiment also provides an opportunity for students to gain proficiency in the organic synthesis techniques of column chromatography, TLC, recrystallization, and melting point determination. Optional characterization of the product by IR, mass spec, and 1H NMR make the experiment applicable for all levels of undergraduate...

The biomimetic synthesis of SNF4435C and SNF4435D, and the total synthesis of the polyene metabolites aureothin, N-acetyl-aureothamine and spectinabilin

Full details of the biomimetic conversion of polyene metabolite spectinabilin ( 5 ) into the isomeric natural products SNF4435C ( 1 ) and SNF4435D ( 2 ) by a cascade of E/ Z-isomerizations and electrocyclizations are reported. Additionally, short total syntheses of the related natural products (±)-aureothin ( 3 ), (±)- N-acetyl-aureothamine ( 4 ) and (±)-spectinabilin ( 5 ) are presented. The key steps in the synthesis of (±)- 3 , (±)- 4 and (±)- 5 are the construction of the tetrahydrofuran motif using a palladium-catalyzed cycloaddition and the ruthenium-catalyzed cross metathesis of alkene 17 to form the common intermediate, boronic ester 24 , which was further transformed using a trans-selective Suzuki coupling with a dibromide and a stereospecific Negishi-type methylation.

A Short Total Synthesis of Aureothin and N-Acetylaureothamine

The total synthesis of the nitrophenyl pyrones, (+/-)-aureothin and (+/-)-N-acetylaureothamine, starting from known 2-ethyl-6-methoxy-3,5-dimethyl-4H-pyran-4-one are described. The key steps involved in the synthesis are the construction of the tetrahydrofuran motif using a palladium-catalyzed cycloaddition and the ruthenium-catalyzed cross-metathesis reaction of an alkenyl boronic ester. [reaction: see text]

Towards "designer" surfaces: functionalisation of self-assembled monolayer (SAM) on colloidal gold by alkene metathesis.

A variety of groups like a Fischer carbene complex, an N-hydroxysuccinimide or a ferrocene derivative have been grafted by ruthenium-catalyzed cross-metathesis reaction with terminal alkene groups on monolayer-protected gold clusters as a mild and convenient strategy to anchor functional molecules.

Effect of a proximal oxygen substituent on the efficacy of ruthenium-catalyzed cross-metathesis and RCM

Ruthenium-catalyzed cross-metathesis of various derivatives of 1,2-dihydroxy-3-butene reveals that cyclic acetals are best suited as substrates compared to acyclic diethers or diacetates, while RCM is relatively insensitive to the presence of allylic or homoallylic hydroxy or acetoxy groups.

ChemInform Abstract: Ruthenium Catalyzed Cross Metathesis with Fluorinated Olefins.

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.

Ruthenium catalysed cross metathesis with fluorinated olefins

The E-selective cross metathesis (CM) of fluorinated olefins with various functionalised alkenes in good to excellent yields is reported.

Extended Alkenyl Glycosides by Ruthenium-Catalyzed Cross-Metathesis Reaction and Application toward Novel C-Linked Pseudodisaccharides.

Grubbs's ruthenium benzylidene catalyst (3) has been successfully applied toward the cross-metathesis reactions of allyl alpha-D-galactopyranoside derivative (4) with a number of olefins. Terminal alkenes possessing a wide range of protecting groups were used as cross-metathetic partners to allow syntheses of glycosides having extended spacers and functionality in the aglycon moieties. The reaction is quite general and the cross-metathesis products (14-21) were obtained in high yields. The strategy has also been applied toward the synthesis of some C-linked pseudodisaccharides from allyl alpha-C-galactoside derivatives (23, 26, and 28) in good yields. In almost all cases, trans-stereoselectivity was found to be good to excellent.

Ruthenium-Catalyzed Yne-Ene Cross Metathesis Binding to Solid Support and Cleavage by Pd0-Catalysis

Ruthenium-Catalyzed Yne-Ene Cross Metathesis Binding to Solid Support and Cleavage by Pd⁰-Catalysis

Ruthenium-Catalyzed Cross-Metathesis of Trisubstituted Vinylsilanes with Light Alkenes

In the cross-metathesis reaction of tri(methyl, ethoxy)vinylsilanes with propene and/or 1-butene catalyzed by RuCl 2 (PPh 3 ) 3 activated in benzene at 115-130 °C, a series of l-alkenylsilanes of general formula CH 3 (CH 2 ) m CH = CHSiMe 3-n (OEt) n , where m =0, 1, and n=0-3 (1-silyl-1-alkenes), as well as of formula CH 2 =C(Me)SiMe 3-n (OEt) n , where n =1, 2 (2-silyl-1-alkenes), were obtained. Additional products determined were allysilanes of general formula CH 2 =CHCH 2 SiMe 3-n (OEt) n and CH 3 CH= CHCH 2 SiMe 3-n (OEt) n , where n=1-3.

Ruthenium-catalysed cross metathesis binding of functionalized olefins to polystyrene resin via a novel allylsilyl linker suitable for electrophilic cleavage

1% Divinylbenzene-crosslinked allyldimethylsilyl polystyrene 1 undergoes highly efficient ruthenium-catalysed cross-metathesis with functionalized terminal olefins and allows electrophilic cleavage of the resulting functionalized allylsilane.