10413-17-9

Upstream product

• 104089-17-0 ethyl 4-(iodozincio)butanoate 
• 100-52-7 benzaldehyde 
• 14371-10-9 (E)-3-phenylpropenal 
• 75424-63-4 5-oxo-5-phenylpentanal 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 79-10-7 acrylic acid 
• 100-42-5 styrene 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 37464-83-8 methyl 5-hydroxy-5-phenylpentanoate 
• 72853-47-5 5-hydroxy-5-phenyl-pent-2-enoic acid methyl ester 
• 108-86-1 bromobenzene 
• 10413-10-2 6-phenyltetrahydro-2H-pyran-2-ol 
• 1327704-47-1 1-phenyl-5-(pyrrolidine-1-yl)pentane-1,5-dione 
• 1453171-99-7 5-((tert-butyldimethylsilyl)oxy)-5-phenyl-1-(pyrrolidin-1-yl)pentan-1-one 

Downstream Products

• 41323-48-2 2-(2-Diethylamino-ethyl)-6-phenyl-tetrahydro-pyran-2-ol 
• 10413-10-2 6-phenyltetrahydro-2H-pyran-2-ol 
• 77613-89-9 2,2-dimethyl-3-benzoyloxycyclohexanone 
• 77613-88-8 ethyl 2,2-dimethyl-3-hydroxy-7-phenyl-7-oxoheptanoate 
• 874656-06-1 5-hydroxy-5-phenyl-pentanoic acid [2-(1H-indol-3-yl)-ethyl]-amide 
• 874656-04-9 5-bromo-5-phenyl-pentanoic acid ethyl ester 
• 81418-17-9 (R)-5-hydroxy-5-phenylpentyl acetate 
• 139527-15-4 (S)-5-hydroxy-5-phenylpentyl acetate 
• 112607-34-8 (6S) 6-phenyltetrahydro-2H-pyran-2-one 
• 112607-33-7 (+)-(R)-δ-(phenyl)-δ-valerolactone 
• 16015-12-6 3,4-dihydro-2-phenyl-2H-pyran 
• 77613-90-2 Benzoic acid (1S,3R)-3-hydroxy-2,2-dimethyl-cyclohexyl ester 
• 77613-92-4 7-Hydroxy-2-methyl-7-phenyl-heptan-3-one 

Relevant academic research and scientific papers

ATP3 and MTP3: Easily Prepared Stable Perruthenate Salts for Oxidation Applications in Synthesis

The Ley–Griffith tetra-n-propylammonium perruthenate (TPAP) catalyst has been widely deployed by the synthesis community, mainly for the oxidation of alcohols to aldehydes and ketones, but also for a variety of other synthetic transformations (e.g. diol cleavage, isomerizations, imine formation and heterocyclic synthesis). Such popularity has been forged on broad reaction scope, functional group tolerance, mild conditions, and commercial catalyst supply. However, the mild instability of TPAP creates preparation, storage, and reaction reproducibility issues, due to unpreventable slow decomposition. In search of attributes conducive to catalyst longevity an extensive range of novel perruthenate salts were prepared. Subsequent evaluation unearthed a set of readily synthesized, bench stable, phosphonium perruthenates (ATP3 and MTP3) that mirror the reactivity of TPAP, but avoid storage decomposition issues.

Copper-catalysed aerobic oxidation of alcohols using fluorous biphasic catalysis

A copper(I) catalysed and TEMPO mediated fluorous biphasic oxidation of primary, secondary, allylic and benzylic alcohols with oxygen in the presence of a bipyridine ligand bearing perfluorinated ponytails is described. High chemoselectivities are observed in the oxidation of substituted cyclohexanols (substituted axial cyclohexanols react 6-8 times faster than the corresponding equatorial cyclohexanols).

CYCLOADDITION OF ISOPROPYLIDENE METHYLENEMALONATE TO ISOSAFROLE AND ANALOGUES

Isopropylidene methylenemalonate (methylene Meldrum's acid) serves as a heterodiene, rather than dienophile in 1:1 adduct formation at room temperature with isosafrole, styrene and p-methoxystyrene.The resultant aryltrioxabicyclodec-1(6)-en-5-one heterocyclic products are degraded under mild hydrolytic conditions to yield the corresponding δ-aryl-δ-valerolactone or 5-arylpent-4-enoic acid.

Catalytic, Enantioselective Vinylogous Mukaiyama Aldol Reaction of Furan-Based Dienoxy Silanes: A Chemodivergent Approach to γ-Valerolactone Flavan-3-ol Metabolites and δ-Lactone Analogues

The asymmetric synthesis of a set of hydroxyphenyl γ-valerolactones was achieved starting from 2-silyloxyfuran and alkoxy-substituted benzaldehydes as common precursors. Key synthesis steps included an enantioselective vinylogous Mukaiyama aldol reaction and a Barton-McCombie deoxygenation. Five enantioenriched γ-valerolactone targets were obtained in 5-6 steps, 18-63% overall yields and 82-98 % ee, paving the way for the straightforward entry to this class of biologically effective and poorly available flavan-3-ol metabolites. In parallel, an unprecedented one-pot reductive ring expansion process was fortuitously discovered, yielding racemic δ-lactone analogues from phenolic butanolide precursors.

Cooperative Catalysis of Samarium Diiodide and Mercaptan in a Stereoselective One-pot Transformation of 5-oxopentanals into δ-lactones

(Matrix Presented) We demonstrate a general method for conversion of various 5-oxopentanals to substituted δ-lactones and 1-oxa-2-decalones by the synergistic catalysis of samarium diiodide and 2-propanethiol (or disulfide). The deliberate use of mercaptan is advantageous to facilitate the catalytic cycle. This method shows high stereoselectivities, and an enantioselective procedure is feasible by using the chiral mercaptan (1R,2S)-1-phenyl-2-(N-acetamido)propanethiol as a promoter.

Visible Light-Driven, Copper-Catalyzed Aerobic Oxidative Cleavage of Cycloalkanones

A visible light-driven, copper-catalyzed aerobic oxidative cleavage of cycloalkanones has been presented. A variety of cycloalkanones with varying ring sizes and various α-substituents reacted well to give the distal keto acids or dicarboxylic acids with moderate to good yields.

Catalytic Redox Chain Ring Opening of Lactones with Quinones to Synthesize Quinone-Containing Carboxylic Acids

Catalytic ring opening of five- to eight-membered lactones with quinones is achieved through a redox chain mechanism. With low loading of a simple metal triflate Lewis acid catalyst and a chain initiator, C-H bonds of many quinones were efficiently functionalized with carboxylic acid-containing side chains. This method also features 100% atom economy and wide substrate scope. A novel route to the anti-asthma drug Seratrodast was developed. Mechanism study suggests that the redox chain reaction likely undergoes a carbocation intermediate.

Cooperative iodine and photoredox catalysis for direct oxidative lactonization of carboxylic acids

A new method for the formation of γ- and δ-lactones from carboxylic acids through direct conversion of benzylic C-H to C-O bonds is described. The reaction is conveniently induced by visible light and relies on a mild cooperative catalysis by the combination of molecular iodine and an organic dye.

Indium-Catalyzed Direct Conversion of Lactones into Thiolactones and Selenolactones in the Presence of Elemental Sulfur and Selenium

The direct conversion of lactones into thiolactones with elemental sulfur (S 8) catalyzed by InCl 3 /PhSiH 3 in a one-pot reaction is described. This catalytic system was successfully applied to the novel preparation of selenolactones from lactones and selenium.

Visible-Light-Induced C-O Bond Formation for the Construction of Five- and Six-Membered Cyclic Ethers and Lactones

Visible-light-induced intramolecular C-O bond formation was developed using 2,4,6-triphenylpyrylium tetrafluoroborate (TPT), which allows the regiocontrolled construction of cyclic ethers and lactones. The reaction is likely to proceed through the single-electron oxidation of the phenyl group, followed by the formation of a benzylic radical, thus preventing a competing 1,5-hydrogen abstraction pathway. Detailed mechanistic studies suggest that molecular oxygen is used to trap the radical intermediate to form benzyl alcohol, which undergoes cyclization. This new approach serves as a powerful platform by providing efficient access to valuable five- and six-membered cyclic ethers and lactones with a unified protocol.