104683-48-9

Upstream product

• 6117-91-5 (E/Z)-2-buten-1-ol 
• 100-52-7 benzaldehyde 
• 96-09-3 styrene oxide 
• 1234421-29-4 (Z)-(3-(butyltellanyl)allyloxy)triiso-propylsilane 
• 6117-80-2 1,4-butenediol 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 930-22-3 epoxybutene 
• 332188-09-7 [2,2-bis(phenylthio)ethyl]dimethyl(1-phenylbut-3-enyloxy)silane 
• 332188-28-0 allyldimethyl[1-phenyl-3,3-bis(phenylthio)propoxy]silane 
• 185559-31-3 1-phenyl-3,3-bis(phenylsulfanyl)propan-1-ol 
• 84216-73-9 2,4-diiodobut-2-en-1-ol 
• 200192-55-8 2,2-dimethyl-7-phenyl-2,3,6,7-tetrahydro-1,2-oxasilepin 
• 1026477-56-4 iodomethyl-dimethyl-(1-phenyl-but-3-enyloxy)-silane 

Downstream Products

• 4660-17-7 rac-6-phenyl-5,6-dihydro-2H-pyran-2-one 

Relevant academic research and scientific papers

Stereoretentive Olefin Metathesis Made Easy: In Situ Generation of Highly Selective Ruthenium Catalysts from Commercial Starting Materials

The in situ preparation of highly stereoretentive ruthenium-based metathesis catalysts is reported. This approach completely avoids the isolation of intermediates and air-sensitive catalysts, thus allowing for the rapid access and evaluation of numerous dithiolate Ru catalysts. A procedure was established to perform cross-metathesis reactions without the use of a glovebox, and on a small scale even Schlenk techniques are not required. Consequently, the chemistry displayed in this report is available to every practicing organic chemist and presents a powerful approach for the identification of new stereoretentive catalysts.

High-value alcohols and higher-oxidation-state compounds by catalytic Z-selective cross-metathesis

Olefin metathesis catalysts provide access to molecules that are indispensable to physicians and researchers in the life sciences. A persisting problem, however, is the dearth of chemical transformations that directly generate acyclic Z allylic alcohols, including products that contain a hindered neighbouring substituent or reactive functional units such as a phenol, an aldehyde, or a carboxylic acid. Here we present an electronically modified ruthenium-disulfide catalyst that is effective in generating such high-value compounds by cross-metathesis. The ruthenium complex is prepared from a commercially available precursor and an easily generated air-stable zinc catechothiolate. Transformations typically proceed with 5.0 mole per cent of the complex and an inexpensive reaction partner in 4-8 hours under ambient conditions; products are obtained in up to 80 per cent yield and 98:2 Z:E diastereoselectivity. The use of this catalyst is demonstrated in the synthesis of the naturally occurring anti-tumour agent neopeltolide and in a single-step stereoselective gram-scale conversion of a renewable feedstock (oleic acid) to an anti-fungal agent. In this conversion, the new catalyst promotes cross-metathesis more efficiently than the commonly used dichloro-ruthenium complexes, indicating that its utility may extend beyond Z-selective processes.

Synthesis and Application of Stereoretentive Ruthenium Catalysts on the Basis of the M7 and the Ru-Benzylidene-Oxazinone Design

A series of new stereoretentive ruthenium catalysts bearing the dithiocatecholate ligand was synthesiszed on the basis of the M7 and Ru-benzylidene-oxazinone design. The activity of the catalysts was tested in ring-opening cross-metathesis reactions, ring

Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction

The ruthenium-catalyzed allylation of aldehydes with allylic pro-nucleophiles has been demonstrated to be an efficient means to form carbon-carbon bonds under mild conditions. The evolution of this reaction from the initial serendipitous discovery to its general synthetic scope is detailed, highlighting the roles of water, CO, and amine in the generation of a more complete catalytic cycle. The use of unsymmetrical allylic pro-nucleophiles was shown to give preferential product formation through the modulation of reaction conditions. Both (E)-cinnamyl acetate and vinyl oxirane were efficiently used to form the anti-branched products (up to >20:1 anti/syn) and E-linear products (up to >20:1 E/Z) in high selectivity with aromatic, α,β-unsaturated, and aliphatic aldehydes, respectively. Attempts to render the reaction enantioselective are highlighted and include enantioenrichment of up to 75:25 for benzaldehyde.

Synthesis and evaluation of (-)-Massoialactone and analogues as potential anticancer and anti-inflammatory agents

(-)-Massoialactone, an α,β-unsaturated δ-lactone isolated from Cryptocarya massoia, and five analogues were synthesized and their antiproliferative and anti-inflammatory activities were evaluated. The lactones were able to mimic the "core" functional grou

Synthesis of substituted α,β-unsaturated δ-lactones from vinyl tellurides

A new approach for the synthesis of α,β-unsaturated δ-lactones, a unit present in many natural products with interesting biological activities is described. The approach was based on the use of a vinyl telluride, and it is complementary to the methods usi

METHOD FOR FORMING ALLYLIC ALCOHOLS

A method of performing a chemical reaction includes reacting an allyl donor and a substrate in a reaction mixture, and forming a homoallylic alcohol in the reaction mixture. The substrate may be an aldehyde or a hemiacetal. The reaction mixture includes a ruthenium catalyst, carbon monoxide at a level of at least 1 equivalent relative to the substrate, and water at a level of at least 1 equivalent relative to the substrate, and an amine at a level of from 0 to 0.5 equivalent relative to the substrate. The reaction mixture may also include a halide, and the equivalents of the amine may be similar to those of the halide. The reacting includes maintaining the reaction mixture at a temperature of at least 40°C. The method may be catalytic in metal, environmentally benign, amenable to large-scale applications, and applicable to a wide range of substrates.

An efficient method for synthesising unsymmetrical silaketals: Substrates for ring-closing, including macrocycle-closing, metathesis

Diisopropylsilyl ethers were activated with N-bromosuccinimide, and reacted with a fluorous-tagged alcohol, to yield tethered substrates for ring-closing metathesis reactions. The Royal Society of Chemistry.

Reaction of allylic-type diindium compounds with electrophiles

Allylic-type diindium reagents were prepared from 3-bromo-1-iodopropene (1a), 3-bromo-1-iodo-1-phenylpropene (1b), or 2,4-diiodobut-2-en-1-ol (1c) with metallic indium, and their successive coupling with electrophiles was examined. The coupling behavior o

Preparation of (Z)-alk-2-ene-1,5-diols by the titanocene(II)-promoted cyclization of thioacetals possessing a terminal carbon-carbon double bond

Titanocene(II)-promoted ring-closing metathesis of the titanium carbene complexes prepared from [2,2-bis(phenylthio)ethyl](but-3-enyloxy)dimethylsilanes or dimethyl(prop-2-enyl)silyl ethers of 3,3-bis(phenythio)propanols gave seven-membered cyclic unsatur