123718-22-9

Upstream product

• 3277-89-2 phenethylmagnesium bromide 
• 78-85-3 2-methylpropenal 
• 33501-90-5 (4-methylpent-3-en-1-yl)benzene 
• 6683-49-4 (4-methylpent-4-en-1-yl)benzene 
• 103-63-9 1-phenyl-2-bromoethane 
• 40463-08-9 2,2-dimethyl-3-(2-phenylethyl)oxirane 
• 104-54-1 3-Phenylpropenol 
• 104-53-0 3-phenyl-propionaldehyde 
• 4119-41-9 1-iodo-3-phenylpropan 
• 557-93-7 2-bromoprop-1-ene 

Downstream Products

• 70388-36-2 (E)-4-methyl-7-phenyl hept-4-ene-oate 
• 76620-37-6 ethyl 4-methyl-7-phenyl-trans-hept-4-enoate 
• 122016-64-2 (E)-7-Methyl-10-phenyl-dec-7-en-5-ol 
• 122016-65-3 2,6-dimethyl-9-phenyl-2,7-nonadien-4-ol 
• 122016-66-4 (E)-1-[1,3]Dithian-2-yl-3-methyl-6-phenyl-hex-3-en-1-ol 
• 122016-62-0 1-Methyl-4-[1-(2-methyl-1-phenethyl-allyloxy)-pentane-1-sulfonyl]-benzene 
• 122016-61-9 1-Methyl-4-[1-(2-methyl-1-phenethyl-allyloxy)-2-phenyl-ethanesulfonyl]-benzene 
• 122016-63-1 (E)-4-Methyl-1-(2-methyl-1-phenethyl-allyloxy)-7-phenyl-1-(toluene-4-sulfonyl)-hept-4-en-2-ol 
• 1449782-77-7 diethyl (1Z,3E)-3-methyl-6-phenylhexa-1,3-dienylphosphonat 
• 40463-09-0 4-methyl-1-phenylpentan-3-one 

Relevant academic research and scientific papers

Electrochemical Nozaki-Hiyama-Kishi Coupling: Scope, Applications, and Mechanism

One of the most oft-employed methods for C-C bond formation involving the coupling of vinyl-halides with aldehydes catalyzed by Ni and Cr (Nozaki-Hiyama-Kishi, NHK) has been rendered more practical using an electroreductive manifold. Although early studies pointed to the feasibility of such a process, those precedents were never applied by others due to cumbersome setups and limited scope. Here we show that a carefully optimized electroreductive procedure can enable a more sustainable approach to NHK, even in an asymmetric fashion on highly complex medicinally relevant systems. The e-NHK can even enable non-canonical substrate classes, such as redox-active esters, to participate with low loadings of Cr when conventional chemical techniques fail. A combination of detailed kinetics, cyclic voltammetry, and in situ UV-vis spectroelectrochemistry of these processes illuminates the subtle features of this mechanistically intricate process.

Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines

This report describes the stereoselective synthesis of 3-azido-tetralins, -chromanes, and -tetrahydroquinolines via a tandem allylic azide rearrangement/Friedel-Crafts alkylation. Exposure of allylic azides with a pendant trichloroacetimidate to catalytic quantities of AgSbF6 proved optimal for this transformation. This cascade successfully differentiates the equilibrating azide isomers, providing products in excellent yield and selectivity (>25 examples, up to 94% yield and >25:1 dr). In many cases, the reactive isomer is only a trace fraction of the equilibrium mixture, keenly illustrating the dynamic nature of these systems. We demonstrate the utility of this process via a synthesis of hasubanan.

General, Simple, and Chemoselective Catalysts for the Isomerization of Allylic Alcohols: The Importance of the Halide Ligand

Remarkably simple IrIIIcatalysts enable the isomerization of primary and sec-allylic alcohols under very mild reaction conditions. X-ray absorption spectroscopy (XAS) and mass spectrometry (MS) studies indicate that the catalysts, with the general formula [Cp*IrIII], require a halide ligand for catalytic activity, but no additives or additional ligands are needed.

Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C-H Activation

α,β-Unsaturated oxime pivalates are proposed to undergo reversible C(sp2)-H insertion with cationic Rh(III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to convert these molecules into piperidines, which are important structural components of numerous pharmaceuticals.

Palladium-catalyzed cross-coupling of unactivated alkenes with acrylates: Application to the synthesis of the C13-C21 fragment of palmerolide A

Diene to meet: A palladium-catalyzed cross-coupling reaction between alkyl-substituted olefins and acrylates gives the corresponding butadienes in moderate yield and stereoselectivity. This atom-economical reaction, which forms C sp 2-C sp 2 bonds, tolerates a wide range of allylic and homoallylic alcohols, and acrylates (see scheme; TIPS =triisopropylsilyl). The methodology was applied to the synthesis of the C13-C21 fragment of palmerolide A.

Palladium-catalyzed cross-coupling of unactivated alkenes with acrylates: Application to the synthesis of the C13-C21 fragment of palmerolide A

Diene to meet: A palladium-catalyzed cross-coupling reaction between alkyl-substituted olefins and acrylates gives the corresponding butadienes in moderate yield and stereoselectivity. This atom-economical reaction, which forms C sp 2-C sp 2 bonds, tolerates a wide range of allylic and homoallylic alcohols, and acrylates (see scheme; TIPS =triisopropylsilyl). The methodology was applied to the synthesis of the C13-C21 fragment of palmerolide A.

New metal-free one-pot synthesis of substituted allenes from enones

(Chemical Equation Presented) A new metal-free, one-pot synthesis of substituted allenes from enones was discovered for the first time, in which a tertiary amine as a base was found to be an effective promoter in such novel transformations. The present synthetic protocol proceeded readily with high compatibility of sensitive functional groups, and it provides a new efficient way to access a series of synthetically important allenes without the use of metallic reagents or catalysts.

Superbase-promoted rearrangement of oxiranes to cyclopropanes

Aryl- and alkenyl substituted oxiranes, when submitted to treatment with superbasic reagents, undergo a highly regio- and stereoselective rearrangement leading to cyclopropylmethanol derivatives. The process can also be applied to mono- and dihydroxy subs

Cyclialkylation of arylalkyl epoxides with solid acid catalysts

Solid acids, such as zeolites and clays, catalyse the intramolecular hydroxyalkylation (cyclialkylation) of several arylalkyl epoxides in moderate to excellent conversions and selectivities. The use of solid acids in these cyclialkylations provides a cleaner, better alternative to conventional Lewis and Bronsted acids, enabling a more facile workup of reaction mixtures and, in several cases, better selectivities.

Lewis Acid Promoted Decomposition of Unsaturated α-Diazo Ketones. 3. Stereochemical Consequences of Polyolefinic Cyclizations Initiated by the α-Diazo Ketone Functionality

This report presents the stereochemical consequences of polyolefinic cyclizations initiated by Lewis acid decomposition of α-diazo ketones.Three diazo ketones (1, 2, and 5) were examined; each was found to undergo a nonstereospecific process leading eithe