197141-42-7

Upstream product

• 1074-12-0 phenylglyoxal hydrate 
• 106-95-6 allyl bromide 
• 7393-43-3 tetraallyl tin 

Downstream Products

• 87258-30-8 6-oxo-6-phenylhexanal 
• 27167-34-6 trans-1-Phenylcyclohexane-1,2-diol 

Relevant academic research and scientific papers

Diastereoselective synthesis of 1-allyl and 1,2-bis(allyl)-1,2- diols: Versatile synthons for substituted tetrahydrofuran derivatives

2-Hydroxyketones and 2-ketoaldehydes undergo indium mediated highly diastereoselective mono and bis- allylation reactions to give respective 1-allyl 2a-c and 1,2-bis (allyl)- 7a-c 1,2 diols. 2a undergoes I2 / NaHCO3 and m-CPBA mediat

Indium-mediated allylation of 1,2-diketones

Indium-mediated allylation of 1,2-dicarbonyl compounds with indium and allylic bromides was achieved in the presence of nBu4NI or NH4Cl as additive to afford mono- and/or diallylated products in good yields.

Intercalation of multiple carbon atoms between the carbonyls of α-diketones

The reaction of open-chain or cyclic α-diketones with specific ω-alkenyl organometallics leads readily under the proper conditions to 1,2-diols bonded to terminal olefinic chains. With 1-phenyl-1,2-propanedione, biacetyl, and cyclohexane-1,2-dione, allylindation in aqueous THF proceeds readily at both adjacent carbonyls. For cyclododecane-1,2-dione, recourse must be made to allylmagnesium bromide for completing the second-stage condensation. Grignard reagents have also served well as reactants for biacetyl monoadducts. In contrast, monoallylated camphorquinone is reluctant to couple to Grignard reagents and reacts only when Barbier-type alkyllithium reactions are applied. The ring closing metatheses of these products have been examined. Where six-membered ring formation operates, cyclization can be performed directly on diols. When larger rings are involved, the diols will react only if structural preorganization capable of facilitating mutual approach of the two double bonds is at play. For this purpose, the prior conversion to a cyclic carbonate holds considerable utility. In the latter setting, saponification must precede the diol cleavage step which has been performed with lead tetraacetate. The latter reagent also exhibits the very beneficial effect of facilitating removal of ruthenium and phosphorus byproducts generated during the metathesis step. This chemistry conveniently lends itself to the controlled intercalation of multiple methylene groups between the carbonyl carbons of readily available α-diketones to deliver linear or cyclic products.

Tandem deployment of indium-, ruthenium-, and lead-promoted reactions. Four-carbon intercalation between the carbonyl groups of open-chain and cyclic α-diketones

(equation presented) An efficient strategy for the conversion of 1,2-diketones into saturated 1,6-diketones and Δ2,3/Δ3,4-unsaturated congeners thereof is reported.

Aqueous Reactions with a Lewis Acid and an Organometallic Reagent. The Scandium Trifluoromethanesulfonate-Catalyzed Allylation Reaction of Carbonyl Compounds with Tetraallyltin

The allylation reaction of a wide variety of carbonyl compounds with tetraallyltin was successfully carried out in aqueous media by using scandium trifluoromethanesulfonate (scandium triflate) as a catalyst.