111183-78-9

Upstream product

• 108-55-4 glutaric anhydride, 
• 1501-04-8 Methyl 4-benzoylbutanoate 
• 17851-47-7 4-(2-phenyl-1,3-dioxolan-2-yl)-1-butanol 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 17202-79-8 1-vinyl-1-cyclobutanol 
• 100-52-7 benzaldehyde 
• 24253-30-3 5-hexen-3-one 
• 43006-71-9 1-(N-Methylanilino)-1-phenylpropen 
• 71-43-2 benzene 
• 381294-88-8 methyl 4-(2-phenyl-1,3-dioxolan-2-yl)butanoate 
• 165613-10-5 5,5-(ethylenedioxy)-5-phenylpentanal 
• 209725-89-3 3-hydroxy-7-ethylenedioxy-7-phenylheptane 
• 75-77-4 chloro-trimethyl-silane 
• 98-88-4 benzoyl chloride 

Downstream Products

• 30708-63-5 2-methyl-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one 

Relevant academic research and scientific papers

Expedient Synthesis of 1,5-Diketones by Rhodium-Catalyzed Hydroacylation Enabled by C-C Bond Cleavage

A rhodium-catalyzed intermolecular hydroacylation reaction of vinyl cyclobutanols with non-chelating aldehydes has been developed. This reaction offers a new and atom-economical approach for the selective preparation of 1,5-diketones in high yields. Experimental data suggest a sequential ring-opening, transfer hydrogenation, and hydroacylation mechanism. We propose that aldehyde decarbonylation is avoided by the formation of a novel rhodium enolate species that also accounts for the compatibility of a broad range of aldehydes and its anti-Markovnikov selectivity.

A convenient synthesis of 1-phenyl-heptane-1,5-dione

An efficient synthesis of the title compound 9 has been developed via Friedel-Craft acylation of benzene and subsequent manipulation of the functionalities of the condensation product 3 for generation of the required 1,5-dione moiety.

Preparation and Reactions of Diorganozincs from Dienic Silyl Enol Ethers

The hydroboration of the dienic silyl enol ethers 1a-d with Et2BH produces organoboranes which are readily converted under mild conditions by a treatment with Et2Zn to the corresponding dialkylzincs 2a-d.These organometallics react after transmetallation with CuCN*2LiCl with various electrophiles affording polyfunctional silyl enol ethers of type 4.In the presence of the chiral catalyst (1R,2R)-bis(trifluoromethanesulfonamido)cyclohexane 6, the dialkylzinc 2b was added to various aldehydes leading to hydroxy silyl enol ethers of type 8 in satisfactory yields (45-77percent) and excellent enantioselectivities (85 to >96percent ee).The chiral products 8 can be oxidatively cyclized using t-BuOOH and catalytic amounts of VO(acac)2 furnishing trisubstituted tetrahydopyrans like 9a,b with high diastereoselectivity.An iodoalkoxylation of 8a affords after HI elimination and Jones oxidation the unsaturated valerolactone 13.

1,5-Dicarbonyl Compounds via Michael-Addition of Deprotonated Enamines and Allylamines to 2-(N-Methylanilino) acrylonitrile

A new method for the synthesis of the title compounds by a onepot, three component, coupling reaction is described.Is consists of the reaction of a homoenolate anion and an enol cation equivalent with subsequent alkylation of an acyl-anion equivalent.Hence the methodology of Umpolung is used in a threefold manner within the reaction sequence.