134679-60-0

Upstream product

• 38300-67-3 1,3,4-Tribromobutane 
• 3240-29-7 1-Phenylpent-4-en-1-one 
• 33574-02-6 cyclopropylmethyl iodide 
• 100-52-7 benzaldehyde 
• 55666-17-6 (1E)-1,4-pentadienylbenzene 
• 5162-44-7 1-bromo-4-butene 
• 7051-34-5 cyclopropylcarbinyl bromide 
• 7103-09-5 4-but-1-enylmagnesium bromide 
• 106-99-0 buta-1,3-diene 
• 96-09-3 styrene oxide 
• 106-95-6 allyl bromide 
• 24850-33-7 allyltributylstanane 
• 1730-25-2 allylmagnesium bromide 
• 50-00-0 formaldehyd 

Downstream Products

• 22927-17-9 4-hydroxy-4-phenyl-butyraldehyde 
• 144222-54-8 dichloroacetic acid 1-phenyl-pent-4-enyl ester 
• 157668-05-8 (1-bromo-pent-4-enyl)-benzene 
• 182195-14-8 5-chloro-5-phenyl-1-pentene 
• 200192-52-5 Allyl-dimethyl-(1-phenyl-pent-4-enyloxy)-silane 
• 351422-26-9 C₁₄H₁₉NOS₂ 
• 1033823-68-5 2-((1-phenylpent-4-en-1-yl)oxy)isoindoline-1,3-dione 
• 16014-91-8 trans-2-(hydroxymethyl)-5-phenyltetrahydrofuran 
• 348598-02-7 dimethyl[(1-phenyl-4-pentenyl)oxy]vinylsilane 
• 144178-31-4 (1R)-1-phenylpent-4-en-1-ol 

Relevant academic research and scientific papers

Catalytic asymmetric mercuriocyclization of γ-hydroxy-cis-alkenes

2-Monosubstituted tetrahydrofurans 2 are obtained with 73-95% ee through the catalytic enantioselective mercuriocyclization of Y-hydroxy-(Z)-alkenes 1 by using Hg(OAc)2 in the presence of HgII complexed with tartrate-derived 4-(2-nap

Nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane

Herein we describe a nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane. A range ofZ-silyl enol ethers are obtained as major isomers due to the process of nickel triggered alkene isomerization. Notably, some specific

Highly Enantioselective Construction of Dihydrooxazines via Pd-Catalyzed Asymmetric Carboetherification

A straightforward synthesis of highly enantioenriched 5,6-dihydro-4H-1,2-oxazines is realized by Pd-catalyzed asymmetric carboetherification of γ,δ-alkenyl oximes with (hetero)aryl and alkenyl halides in the presence of a commercially available bisphosphine ligand. The enantioenriched products can be facilely converted to functionalized alcohols with high fidelity of chiral transfer.

Nickel-Catalyzed Hydroarylation of in Situ Generated 1,3-Dienes with Arylboronic Acids Using a Secondary Homoallyl Carbonate as a Surrogate for the 1,3-Diene and Hydride Source

The nickel-catalyzed hydroarylation of 1,3-dienes with arylboronic acids using a secondary homoallyl carbonate as a surrogate for the 1,3-diene and hydride source has been developed. The synthetic strategy allowed an efficient access to a wide array of hydroarylation products in high yields with high functional group compatibility without the use of an external hydride source. Mechanistic experiments indicated that the alkene-directed oxidative addition and subsequent β-hydride elimination would be a critical process in this transformation.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE SUBSTITUTED TETRAHYDROFURAN DERIVATIVE

PROBLEM TO BE SOLVED: To provide a synthesis method for achieving asymmetric synthesis of substituted tetrahydrofuran derivative, especially 2-substituted-5-substituted methyltetrahydrofuran derivative. SOLUTION: Provided are a method, in which an optically active substituted tetrahydrofuran derivative is synthesized from optically active alcohol in accordance with bromoetherification reaction by oxygen oxidation of bromide ion; and a method, in which, characterized, an optically active alcohol is synthesized by performing an enantioselective hydrogen transfer type reaction using an optically active ruthenium-catalyst from butenyl ketone. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Copper-Catalyzed Cope-Type Hydroamination of Nonactivated Olefins toward Cyclic Nitrones: Scope, Mechanism, and Enantioselective Process Development

The catalytic synthesis of cyclic nitrones, an important type of functional molecules for both synthetic chemistry and related fields, remains underdeveloped. Herein we report the copper-catalyzed Cope-type hydroamination of oximes with pendant nonactivated olefins, which enables facile access to a series of five- and six-membered cyclic nitrones under mild conditions. In this study, heterocycle-tethered oximes were employed in the Cope-type hydroamination reaction for the first time. High enantioselectivity was achieved for carbon-tethered γ,δ-vinyl oximes to afford enantioenriched five-membered cyclic nitrones. The results of preliminary mechanistic studies indicate a mononuclear catalytic species and a unified catalytic pathway over a large temperature range.

Bromoetherification of Alkenyl Alcohols by Aerobic Oxidation of Bromide: Asymmetric Synthesis of 2-Bromomethyl 5-Substituted Tetrahydrofurans

An asymmetric synthesis of 2-bromomethyl-5-substituted tetrahydrofurans via a chiral-ruthenium-catalyzed transfer hydrogenation of 3-butenyl ketones and bromoetherification of chiral pentenyl alcohols was developed. The inhibition of some side reactions furnished the desired products in high yields with high enantioselectivities. In addition, chiral pentenyl alcohols bearing electron-donating groups triggered substrate racemization in the aerobic bromoetherification.

Cobalt-Catalyzed Stereoselective Synthesis of 2,5- trans-THF Nitrile Derivatives as a Platform for Diversification: Development and Mechanistic Studies

A straightforward protocol integrating a sustainable approach for the synthesis of new 2,5-trans-THF nitrile derivatives enabling an easy diversification of its side chain scaffolds is described. The reaction tolerated different aromatic and alkyl substit

Dual cobalt-copper light-driven catalytic reduction of aldehydes and aromatic ketones in aqueous media

We present an efficient, general, fast, and robust light-driven methodology based on earth-abundant elements to reduce aryl ketones, and both aryl and aliphatic aldehydes (up to 1400 TON). The catalytic system consists of a robust and well-defined aminopyridyl cobalt complex active for photocatalytic water reduction and the [Cu(bathocuproine)(Xantphos)](PF6) photoredox catalyst. The dual cobalt-copper system uses visible light as the driving-force and H2O and an electron donor (Et3N or iPr2EtN) as the hydride source. The catalytic system operates in aqueous mixtures (80-60% water) with high selectivity towards the reduction of organic substrates (>2000) vs. water reduction, and tolerates O2. High selectivity towards the hydrogenation of aryl ketones is observed in the presence of terminal olefins, aliphatic ketones, and alkynes. Remarkably, the catalytic system also shows unique selectivity for the reduction of acetophenone in the presence of aliphatic aldehydes. The catalytic system provides a simple and convenient method to obtain α,β-deuterated alcohols. Both the observed reactivity and the DFT modelling support a common cobalt hydride intermediate. The DFT modelled energy profile for the [Co-H] nucleophilic attack to acetophenone and water rationalises the competence of [CoII-H] to reduce acetophenone in the presence of water. Mechanistic studies suggest alternative mechanisms depending on the redox potential of the substrate. These results show the potential of the water reduction catalyst [Co(OTf)(Py2Tstacn)](OTf) (1), (Py2Tstacn = 1,4-di(picolyl)-7-(p-toluenesulfonyl)-1,4,7-triazacyclononane, OTf = trifluoromethanesulfonate anion) to develop light-driven selective organic transformations and fine solar chemicals.

Design, synthesis, and evaluation of a novel series of macrocyclic inhibitors of norovirus 3CL protease

Norovirus infections have a major impact on public health worldwide, yet there is a current dearth of norovirus-specific therapeutics and prophylactics. This report describes the discovery of a novel class of macrocyclic inhibitors of norovirus 3C-like pr