77614-49-4

Upstream product

• 827-69-0 (E)-4-phenyl-3-penten-2-one 
• 57094-30-1 2-methyl-4-phenylpentanal 
• 17913-10-9 1-methyl-3-phenyl-butanal 
• 591-50-4 iodobenzene 
• 1569-50-2 3-penten-2-ol 
• 1825-14-5 pentane-1,3-diol 
• 5182-36-5 4-phenyl-2,4,6-trimethyl-1,3-dioxane 
• 16251-77-7 3-Phenylbutyraldehyde 
• 676-58-4 methylmagnesium chloride 
• 917-54-4 methyllithium 
• 219547-28-1 4-iodopentan-2-ol 

Downstream Products

• 17913-10-9 1-methyl-3-phenyl-butanal 
• 92036-21-0 3-methyl-5-phenyl-hexanoic acid 

Relevant academic research and scientific papers

Capturing the Monomeric (L)CuH in NHC-Capped Cyclodextrin: Cavity-Controlled Chemoselective Hydrosilylation of α,β-Unsaturated Ketones

The encapsulation of copper inside a cyclodextrin capped with an N-heterocyclic carbene (ICyD) allowed both to catch the elusive monomeric (L)CuH and a cavity-controlled chemoselective copper-catalyzed hydrosilylation of α,β-unsaturated ketones. Remarkably, (α-ICyD)CuCl promoted the 1,2-addition exclusively, while (β-ICyD)CuCl produced the fully reduced product. The chemoselectivity is controlled by the size of the cavity and weak interactions between the substrate and internal C?H bonds of the cyclodextrin.

Cobalt-salen complex-catalyzed oxidative generation of alkyl radicals from aldehydes for the preparation of hydroperoxides

Catalytic generation of alkyl radicals from aldehydes via oxidative deformylation was realized using a cobalt-salen complex with H2O 2. The deformylation was thought to proceed through homolytic cleavage of peroxohemiacetal intermediates to provide even primary alkyl radicals under mild conditions. Variously substituted and functionalized hydroperoxides were obtained from corresponding aldehydes in good yield.

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.

Baeyer-Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters

The application of three BVMOs for the enantioselective oxidation of 3-phenylbutan-2-ones with different substituents in the aromatic moiety is described. By choosing the appropriate biocatalyst and substrate combination, chiral ketones and esters can be obtained with excellent enantiopurities. This methodology could also be applied to the resolution of racemic α-alkyl benzylketones with longer alkyl chains as well as with two substituted α-substituted benzylacetones. A kinetic analysis revealed that the BVMOs studied effectively convert all tested compounds showing that the enzymes are tolerant towards the substrate structure while being highly enantioselective. These properties render BVMOs as valuable biocatalysts for the preparation of compounds with high interest in organic synthesis.

Highly chemo- And enantioselective hydrogenation of linear α,β-unsaturated ketones

A study was conducted to report the synthesis of sulfoximine-derived P,N-ligands and their applications in indium-catalyzed asymmetric hydrogenation reactions. Investigations were conducted using linear β,β- disubstituted 1,3-diphenyl-2-butenone as model substrate and iridium, having a ketonic phenyl group and two alkyl substituents at the olefinic β-positions. Methyl ketone with β-methyl and β-phenyl substituent was also applied in the investigations.

4-Phenylpentan-2-ol as a fragrance and flavouring

The use of 4-phenylpentan-2-ol (I) as a fragrance or flavouring is described.

Stereoselective radical Aryl migration reactions from sulfur to carbon

Stereoselective aryl migration reactions from sulfur in sulfonates and sulfonamides to C-centered radicals are reported. The 1,5-aryl migration from sulfur to differently substituted C-centered radicals could be performed with high yields and selectivities. Functionalized aryl groups could also be transferred by this new method. A model to explain the stereochemical outcome of the reaction is presented and some mechanistic aspects of this reaction are discussed. Aryl migration reactions from sulfur in sulfinates to carbon radicals were less efficient, and the corresponding migrations in aryl sulfoxides were not observed at all. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Stereoselective radical aryl migration from silicon to carbon

Highly diastereoselective radical 1,5 phenyl migration reactions from silicon in diarylsilyl ethers to various C-centered radicals to form the corresponding 3-phenylated alcohols are described. Functionalized aryl groups can also be transferred. The effect of the variation of the attacking radical on the aryl transfer reaction is discussed. Best results are obtained for the phenyl migration to nucleophilic secondary alkyl radicals, where high yields (up to 81%) and high selectivities (up to 95% ds) have been obtained. The mechanism of the process is discussed and a model to explain the stereochemical outcome of the reaction is presented. Finally, stereoselective 1,4 aryl migration reactions from Si to C, including a new method for the α- arylation of esters, are presented.

The S(H)i reaction at silicon - A new entry into cyclic alkoxysilanes

A new mild radical method for the preparation of cyclic five-membered alkoxysilanes is reported. This method comprises an intramolecular homolytic substitution reaction at silicon (S(H)i). Various leaving groups (SiMe3, GeMe3, SnMe3) were tested in the homolytic substitution reaction. We found that high yields were only obtained for silanes bearing a trimethyl-stannyl functionality as leaving group in the S(H)i reaction. Rate constants for the cyclization reaction were estimated by conducting standard competition experiments. Based on the kinetic data, more elaborate reaction sequences such as radical addition reactions with a subsequent S(H)i step were carried out. Stereoselective cyclization reactions were also investigated. Excellent 1,2 diastereoselectivities were observed. The products of the S(H)i reaction, cyclic alkoxysilanes, can easily be converted to the corresponding diol derivatives by Tamao-Fleming oxidation as demonstrated for several examples.