86983-95-1

Upstream product

• 920-39-8 isopropylmagnesium bromide 
• 104-55-2 3-phenyl-propenal 
• 3160-32-5 (1E)-4-methyl-1-phenylpent-1-en-3-one 
• 1068-55-9 isopropylmagnesium chloride 
• 14371-10-9 (E)-3-phenylpropenal 
• 536-74-3 phenylacetylene 
• 139313-56-7 4-methyl-1-phenyl-pent-1-yn-3-ol 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 563-80-4 3-methyl-butan-2-one 
• 100-52-7 benzaldehyde 
• 1888-75-1 isopropyllithium 
• 78-83-1 2-methyl-propan-1-ol 
• 103-64-0 bromostyrene 
• 78-84-2 isobutyraldehyde 

Downstream Products

• 3160-32-5 (1E)-4-methyl-1-phenylpent-1-en-3-one 
• 109801-04-9 trans-1-(1-hydroxy-2-methylpropyl)-2-phenylcyclopropane 
• 220089-23-6 trans-(R)-4-methyl-1-phenyl-1-penten-3-ol 
• 473758-24-6 triethyl{[(2E)-1-isopropyl-3-phenylprop-2-enyl]oxy}silane 
• 1314802-08-8 [(1E)-3-azido-4-methyl-1-penten-1-yl]-benzene 
• 1314802-24-8 (2E)-N-(4-methoxybenzyloxy)-3-(1-((E)-4-methyl-1-phenylpent-1-en-3-yl)-1H-1,2,3-triazol-4-yl)acrylamide 
• 1314801-85-8 (2E)-N-hydroxy-3-(1-((E)-4-methyl-1-phenylpent-1-en-3-yl)-1H-1,2,3-triazol-4-yl)acrylamide 
• 39491-73-1 (E)-(4-methylpenta-1,3-dien-1-yl)benzene 
• 1401009-22-0 C₁₂H₁₅F 
• 1401009-10-6 C₁₆H₂₅O₃PS 

Relevant academic research and scientific papers

Asymmetric transfer hydrogenation of cycloalkyl vinyl ketones to allylic alcohols catalyzed by ruthenium amido complexes

A chemoselective 1,2-reduction of cycloalkyl vinyl ketones via asymmetric transfer hydrogenation is described. The reduction proceeded smoothly with a chiral diamine ruthenium complex as a catalyst and a HCOOH-NEt3 azeotrope as both a hydrogen source and solvent under mild conditions. A wide range of 1-cycloalkyl chiral allylic alcohols were obtained in good yields and up to 87% ee. It was found that the alkyl group plays an important role in the enantioselectivity.

Gold-catalyzed [4+2] Annulations of Dienes with Nitrosoarenes as 4 π Donors: Nitroso-Povarov Reactions

This work reports the first success of the nitroso-Povarov reaction, involving gold-catalyzed [4+2] annulations of nitrsoarenes with substituted cyclopentadienes. In this catalytic sequence, nitrosoarenes presumably attack gold-π-dienes by a 1,4-addition pathway, generating allylgold nitrosonium intermediates to complete an intramolecular cyclization. Acyclic dienes are also applicable substrates, and affording oxidative nitroso-Povarov products.

Synthesis of Chiral α,β-Unsaturated γ-Amino Esters via Pd-Catalyzed Asymmetric Allylic Amination

A Pd-catalyzed asymmetric allylic amination of 4-substituted 2-acetoxybut-3-enoates with amines has been developed for the regiospecific synthesis of chiral α,β-unsaturated γ-amino esters. The desired chiral aminated products can be obtained in up to 98%

Kinetic Resolution of Racemic Allylic Alcohols by Catalytic Asymmetric Substitution of the OH Group with Monosubstituted Hydrazines

A new strategy has been established for the kinetic resolution of racemic allylic alcohols through a palladium/sulfonyl-hydrazide-catalyzed asymmetric OH-substitution under mild conditions. In the presence of 1 mol % [Pd(allyl)Cl]2, 4 mol % (S)-SegPhos, and 10 mol % 2,5-dichlorobenzenesulfonyl hydrazide, a range of racemic allylic alcohols were smoothly resolved with selectivity factors of more than 400 through an asymmetric allylic alkylation of monosubstituted hydrazines under air at room temperature. Importantly, this kinetic resolution process provided various allylic alcohols and allylic hydrazine derivatives with high enantiopurity.

Electrophilic Cyanation of Boron Enolates: Efficient Access to Various β-Ketonitrile Derivatives

The highly efficient electrophilic cyanation of boron enolates using readily available cyanating reagents, N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) and p-toluenesulfonyl cyanide (TsCN), is reported. Various β-ketonitriles were prepared by this new protocol, which has a remarkably broad substrate scope compared to existing methods. The present method also allowed efficient synthesis of β-ketonitriles containing a quaternary α-carbon center. In addition, a preliminary result with the use of a chiral boron enolate for the enantioselective cyanation reaction is described.

Pincer-Nickel-Catalyzed Allyl-Aryl Coupling between Allyl Methyl Ethers and Arylzinc Chlorides

The P,N,N-pincer nickel complex [Ni(Cl){N(2-Ph2PC6H4)(2′-Me2NC6H4)}]-catalyzed allyl-aryl coupling was studied. The reaction of allyl methyl ethers, including (1-methoxyallyl)arenes and (3-methoxyprop-1-en-1-yl)arenes, with arylzinc chlorides afforded linear (E)-alkenes in high yields, whereas the reaction of (E)-1-methoxytridec-2-ene with p-Me2NC6H4ZnCl generated a mixture of linear and branched alkenes.

Non-enzymatic acylative kinetic resolution of primary allylic amines

A non-enzymatic acetyl transfer-based kinetic resolution of primary allylic amines is reported. The process involves the use of (1S,2S)-1 in conjunction with a supported ammonium salt and affords the corresponding enantio-enriched N-acetylated allylic ami

Structure-based optimization of click-based histone deacetylase inhibitors

Previously, we reported a click-chemistry based approach to the synthesis of a novel class of histone deacetylase (HDAC) inhibitors [1]. The lead compound NSC746457 was found to be as potent as SAHA (Vorinostat). Further optimization of NSC746457 by using

Chemoselective conjugate reduction of α,β-unsaturated ketones catalyzed by rhodium amido complexes in aqueous media

Although a notable feature of Noyori's Ru-TsDPEN complex is that the transfer hydrogenation reaction is highly chemoselective for the C-O functional group and tolerant of alkenes, our early report indicated that the chemoselectivity could be switched from C-O to C-C bonds in the transfer hydrogenation of activated α,β-unsaturated ketones. Now we have found that a variety of α,β-unsaturated ketones, even without other electron-withdrawing functional groups, could be reduced on the alkenic double bonds with high selectivities employing amido-rhodium hydride complex in aqueous media, and up to 100% chemoselectivity has been achieved. It is notable that the chemoselectivity was improved significantly on going from organic solvent to water. Moreover, a 1,4-addition mechanism has been proposed on the basis of the corresponding experimental details and computational analysis.

Indium-promoted chemo- and diastereoselective allylation of α,β-epoxy ketones with potassium allyltrifluoroborate

A practical method for the chemo- and diastereoselective allylation of α,β-epoxy ketones has been developed by using the convenient air and moisture stable reagent potassium allyltrifluoroborate. Indium metal was found to promote addition in stoichiometric or catalytic amounts, to afford α,β-epoxyhomoallylic tertiary alcohols in high yields and diastereoselectivities, without competing ring-scission of the epoxide.