93404-36-5

Upstream product

• 81187-86-2 ethyl 3-(4-chlorophenyl)-2-butenoate 
• 21757-98-2 ethyl (E)-3-(4-chlorophenyl)-2-butenoate 
• 99-91-2 para-chloroacetophenone 

Downstream Products

• 132533-13-2 3-(4-Chloro-phenyl)-2-hydroperoxy-but-3-en-1-ol 
• 648425-34-7 (2E)-3-(4'-chlorophenyl)but-2-en-1-yl chloride 
• 1374647-42-3 (-)-1-chloro-4-(3-methylnon-1-en-3-yl)benzene 
• 1047082-72-3 (E)-1’-chloro-4’-(4-bromobut-2-en-2-yl)benzene 
• 1374647-41-2 (-)-1-chloro-4-(3-methylhept-1-en-3-yl)benzene 
• 23853-78-3 1-chloro-4-(1-methylprop-2-en-1-yl)benzene 
• 132533-25-6 (3R,6R)-6-[1-(4-Chloro-phenyl)-vinyl]-3-(4-methoxy-phenyl)-[1,2,4]trioxane 
• 132533-21-2 3-[1-(4-Chloro-phenyl)-vinyl]-1,2,5-trioxa-spiro[5.5]undecane 
• 132533-17-6 6-[1-(4-Chloro-phenyl)-vinyl]-3,3-dimethyl-[1,2,4]trioxane 
• 273377-20-1 2,2,2-trichloro-N-[1-(4-chloro-phenyl)-1-methyl-allyl]-acetamide 

Relevant academic research and scientific papers

Palladium-Catalyzed Allyl-Allyl Reductive Coupling of Allylamines or Allylic Alcohols with H2as Sole Reductant

Catalytic carbon-carbon bond formation building on reductive coupling is a powerful method for the preparation of organic compounds. The identification of environmentally benign reductants is key for establishing an efficient reductive coupling reaction. Herein an efficient strategy enabling H2 as the sole reductant for the palladium-catalyzed allyl-allyl reductive coupling reaction is described. A wide range of allylamines and allylic alcohols as well as allylic ethers proceed smoothly to deliver the C-C coupling products under 1 atm of H2. Kinetic studies suggested that the dinuclear palladium species was involved in the catalytic cycle.

Rh-Catalyzed Asymmetric Hydrogenation of β-Branched Enol Esters for the Synthesis of β-Chiral Primary Alcohols

An asymmetric hydrogenation of β-branched enol esters has been developed for the first time, providing a new route for the synthesis of β-chiral primary alcohols. Using a (S)-SKP-Rh complex bearing a large bite angle and enol ester substrates possessing an O-fomyl directing group, the desired products were obtained in quantitative yields and with excellent enantioselectivities.

Copper(I)-Catalyzed Allylic Substitutions with a Hydride Nucleophile

An easily accessible copper(I)/N-heterocyclic carbene (NHC) complex enables a regioselective hydride transfer to allylic bromides, an allylic reduction. The resulting aryl- and alkyl-substituted branched α-olefins, which are valuable building blocks for synthesis, are obtained in good yields and regioselectivity. A commercially available silane, (TMSO)2Si(Me)H, is employed as hydride source. This protocol offers a unified alternative to the established metal-catalyzed allylic substitutions with carbon nucleophiles, as no adaption of the catalyst to the nature of the nucleophile is required.

Iridium-catalyzed asymmetric hydrogenation of 3,3-disubstituted allylic alcohols in ethereal solvents

Ir-phosphinomethyl-oxazoline complexes have been identified as efficient, highly enantioselective catalysts for the asymmetric hydrogenation of 3,3-disubstituted allylic alcohols and related homoallylic alcohols. In contrast to other N,P ligand complexes, which require weakly coordinating solvents, such as dichloromethane, these catalysts perform well in more ecofriendly THF or 2-MeTHF. Their synthetic potential was demonstrated with the formal total synthesis of four bisabolane sesquiterpenes. Particularly high enantioselectivity values in the asymmetric hydrogenation of 3,3-disubstituted allylic alcohols and related homoallylic alcohols have been achieved with Ir-phosphinomethyloxazoline catalysts. In contrast to other N,P-ligand complexes, which require weakly coordinating solvents, such as CH 2Cl2, these catalysts perform well in more ecofriendly THF or 2-MeTHF (see scheme; CODa =a 1,5-cyclooctadiene). Copyright

Enantioselective synthesis of tertiary and quaternary stereogenic centers: Copper/phosphoramidite-catalyzed allylic alkylation with organolithium reagents

An efficient and highly enantioselective copper-catalyzed allylic alkylation of disubstituted allyl halides with primary and secondary organolithium reagents using phosphoramidite ligands is reported. The use of trisubstituted allyl bromides allows, for the first time, the enantioselective synthesis of all-carbon quaternary stereogenic centers with these reactive organometallic reagents.

Enantioselective synthesis of allylboronates bearing a tertiary or quaternary B-substituted stereogenic carbon by NHC-Cu-catalyzed substitution reactions

Allylic substitutions that afford α-substituted allylboronates bearing B-substituted tertiary or quaternary carbon stereogenic centers are presented. C-B bond-forming reactions, catalyzed by chiral bidentate Cu-NHC complexes, are performed in the presence of commercially available bis(pinacolato)diboron. Transformations proceed in high yield (up to >98%) and site selectivity (>98% SN2′), and in up to >99:1 enantiomer ratio. Trans- or cis-disubstituted alkenes can be used; alkyl- (linear as well as branched) and aryl-trisubstituted allylic carbonates serve as effective substrates. Allylboronates that bear a quaternary carbon center are air-stable and can be easily purified by silica gel chromatography; in contrast, secondary allylboronates cannot be purified in the same manner and are significantly less stable. Oxidation of the enantiomerically enriched products furnishes secondary or tertiary allylic alcohols, valuable small molecules that cannot be easily obtained in high enantiomeric purity by alternative synthesis or kinetic resolution approaches.

Synthesis of novel diazatricyclodecanes (DTDs). Effects of structural variation at the C3′ allyl end and at the phenyl ring of the cinnamyl chain on μ-receptor affinity and opioid antinociception

Two series of analogues of 9-propionyl-10-cinnamyl-9,10-diazatricyclo[4.2.1.12,5]decane (1a) and 2-propionyl-7-cinnamyl-2,7-diazatricyclo[4.4.0.03,8]decane (2a), in which the cinnamyl moiety was replaced by various aralkenyl chains,