95465-44-4

Upstream product

• 108-86-1 bromobenzene 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 127084-23-5 1-(2-Methyl-propenyltellanyl)-butane 
• 100-52-7 benzaldehyde 
• 513-37-1 2-methylprop-1-enyl chloride 
• 22379-62-0 potassium benzyloxide 
• 3017-69-4 2-methyl-1-propenylbromide 
• 591-51-5 phenyllithium 
• 38614-36-7 2-methylpropen-1-ylmagnesium bromide 
• 100-58-3 phenylmagnesium bromide 
• 98-86-2 acetophenone 
• 43108-74-3 3-hydroxy-3-methyl-1-phenyl-1-butanone 

Downstream Products

• 68036-69-1 (E)-2-methyl-4-phenyl-1,3-butadiene 
• 143372-44-5 C₁₈H₂₀O 
• 5650-07-7 3-methyl-1-phenyl-but-2-en-1-one 
• 38968-65-9 2-(benzyloxy)-2-phenylacetaldehyde 
• 143372-31-0 ethyl 4-(benzyloxy)-2-(ethoxycarbonyl)-4-phenyl-2-butenoate 
• 143372-33-2 2-(2-Benzyloxy-1-methyl-2-phenyl-ethyl)-malonic acid diethyl ester 
• 1204595-23-2 (1-azido-3-methylbut-2-en-1-yl)benzene 
• 1610543-01-5 3,3-dimethyl-1-phenylhex-5-en-1-one 
• 1197215-35-2 C₁₄H₂₀O 
• 1610543-12-8 C₁₄H₂₀O 
• 1610543-22-0 C₁₅H₂₂O 
• 1610543-23-1 C₁₇H₂₆O₂ 
• 1610543-61-7 C₁₄H₁₈ 
• 21919-51-7 3-methyl-1-phenyl-buta-1,3-diene 

Relevant academic research and scientific papers

Regio- and diastereoselective ene reaction of 4-phenyl-1,2,4- triazoline-3,5-dione with chiral allylic alcohols and their derivatives

Chiral allylic alcohols 1a-e reacted with 4-phenyl-1,2,4-triazoline- 3,5-dione (PTAD) in CH2Cl2 to produce 3-amino-1-alken-4-ols 2 and 3 in 78- 89% yields, with 68-90% diastereomeric excess (de) in favor of the threo isomer. Chiral allylic ethers 1f,g and acetates 1h,i gave similar yields but lower de (34-66%). Reaction of allylic alcohols 6a-e with PTAD in CH2Cl2 produced 1,3-regioisomers 7 and 8 exclusively in 33-65% yields without apparent diastereoselectivity, except when R1 was a Bu(t) group, in which case only syn product 7 was formed. However, when 6a or 6c was subjected to reaction with PTAD in a polar solvent, up to 88% de was observed. Reaction of allylic ethers 6f,g and acetates 6h,i with PTAD in CH2Cl2 also produced 7 and 8 exclusively with improved yields (56-96%) and diastereoselectivity (50- 100% de in favor of the syn isomer).

KOtBu/DMSO Catalytic System for Isomerization of Allylic Alcohols to Ketones

The isomerization of allylic alcohols is an important reaction because it can afford carbonyl compounds in an atom-economical manner. Although base-catalyzed methods are more desirable than those using transition-metal catalysts from both the economic and environmental points of view, these methods have several drawbacks, such as narrow substrate scope and high catalyst loading. This paper reports the development of an efficient KOtBu/DMSO catalytic system suitable for the isomerization of a broad range of allylic alcohols with good yields, to which previously reported systems could not be applied. This catalytic system was successfully applied to a tandem allylic isomerization/electrophilic trapping reaction, thereby highlighting its synthetic utility.

Visible Light Mediated Photocatalytic N-Radical Cascade Reactivity of O,δ-Unsaturated N-Arylsulfonylhydrazones: A General Approach to Structurally Diverse Tetrahydropyridazines

Tetrahydropyridazines are of particular interest for their versatility as intermediates in organic synthesis and display pharmacological activity in several domains. Here, we describe the photocatalytic synthesis of different tetrahydropyridazines starting from O,δ-unsaturated N-arylsulfonylhydrazones. Simple structural changes of substrates result into three different pathways beginning from a common N-hydrazonyl radical, which evolves through a domino carboamination/dearomatization, a HAT process, or a photoinduced radical Smiles rearrangement to afford diverse tetrahydropyridazines. All reactions are carried out in very mild conditions, and the quite inexpensive [Ru(bpy)3]Cl2 is used as the catalyst. Preliminary mechanism studies are presented, among them luminescence and electrochemical characterization of the involved species. Computational studies allow to rationalize the mechanism in accord with the experimental findings.

One-Pot Conversion of Allylic Alcohols to α-Methyl Ketones via Iron-Catalyzed Isomerization-Methylation

A one-pot iron-catalyzed conversion of allylic alcohols to α-methyl ketones has been developed. This isomerization-methylation strategy utilized a (cyclopentadienone)iron(0) carbonyl complex as precatalyst and methanol as the C1 source. A diverse range of allylic alcohols undergoes isomerization-methylation to form α-methyl ketones in good isolated yields (up to 84% isolated yield).

Nickel-Catalyzed Chemoselective Asymmetric Hydrogenation of α,β -Unsaturated Ketoimines: An Efficient Approach to Chiral Allylic Amines

An efficient synthetic route to chiral allylic amines has been developed by nickel/(S,S)-Ph-BPE complex catalyzed chemoselective asymmetric hydrogenation of α,β-unsaturated ketoimines. Varieties of α,β-unsaturated ketoimines have been well tolerated in this transformation to give chiral allylic amines with high yields and excellent ee values (up to 99% yield, up to 99% ee). A gram-scale reaction with 0.2 mol % catalyst loading has also been achieved.

Synthesis, Characterization, Cytotoxicity, and Antibacterial Properties of trans-γ-Halo-δ-lactones

A new four-step pathway for the synthesis of γ-halo-δ-lactones is described from simple, commercially available substrates: aryl bromides and 3-methyl crotonaldehyde. The halogenolactonization reaction of β,δ-substituted, γ,δ-unsaturated carboxylic acid 4

Diastereo- and Enantioselective Formal [3 + 2] Cycloaddition of Cyclopropyl Ketones and Alkenes via Ti-Catalyzed Radical Redox Relay

We report a stereoselective formal [3 + 2] cycloaddition of cyclopropyl ketones and radical-acceptor alkenes to form polysubstituted cyclopentane derivatives. Catalyzed by a chiral Ti(salen) complex, the cycloaddition occurs via a radical redox-relay mechanism and constructs two C-C bonds and two contiguous stereogenic centers with generally excellent diastereo- and enantioselectivity.

Tuning the Reactivity of Functionalized Diallylic Alcohols: Br?nsted versus Lewis Acid Catalysis

The chemodivergent reactivity of bifunctional, enol thioether-containing diallylic alcohols in acidic medium is disclosed, highlighting the difference between strong Lewis acid and mild Br?nsted acid catalysis. In the presence of bismuth(III) triflate, allylic alcohol activation affords diversely substituted cyclopentenones in a Nazarov-type electrocyclization, whereas activation of the thioenol ether by p-toluenesulfonic acid provides an entry to α-sulfenylated β,γ-unsaturated ketones. Both methods represent a facile access to the corresponding products under mild conditions, using inexpensive and non-toxic catalytic systems.

Ruthenium-catalyzed tandem-isomerization/asymmetric transfer hydrogenation of allylic alcohols

A one-pot procedure for the direct conversion of racemic allylic alcohols to enantiomerically enriched saturated alcohols is presented. The tandem-isomerization/ asymmetric transfer hydrogenation process is efficiently catalyzed by [{Ru(p-cymene)Cl2}2] in combination with the a-amino acid hydroxyamide ligand 1, and performed under mild conditions in a mixture of ethanol and THF. The saturated alcohol products are isolated in good to excellent chemical yields and in enantiomeric excess up to 93%.

Enantiospecific intramolecular heck reactions of secondary benzylic ethers

Enantioenriched methylenecyclopentanes are synthesized by stereospecific, nickel-catalyzed Heck cyclizations of secondary benzylic ethers. The reaction proceeds in high yield and enantiospecificity for benzylic ethers of both π-extended and simple arenes. Ethers with pendant 1,2-disubstituted olefins form trisubstituted olefins with control of both absolute configuration and alkene geometry. Diastereoselective synthesis of a polycyclic furan is demonstrated.