7661-44-1

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 34713-70-7 2-Phenylpropanal 
• 109-72-8 n-butyllithium 
• 39575-97-8 4,4,6-trimethyl-2-(1-phenyl-ethyl)-5,6-dihydro-4H-[1,3]oxazine 
• 7661-43-0 2-Phenylheptan-3-ol 
• 17229-74-2 2,4-diphenyl-2H-isoxazol-5-one 
• 74-88-4 methyl iodide 
• 110-59-8 pentanonitrile 
• 7695-69-4 bis(phenylthio)methylbenzene 
• 1068-55-9 isopropylmagnesium chloride 
• 25870-62-6 1-phenyl-2-hexanone 
• 100-42-5 styrene 
• 71-41-0 pentan-1-ol 
• 110-62-3 pentanal 

Downstream Products

• 97234-89-4 (Z)-2-phenyl-3-trimethylsilyloxy-3-heptene 
• 97234-87-2 (E)-2-phenyl-3-trimethylsiloxy-3-heptene 
• 97234-85-0 (E)-2-phenyl-3-trimethylsilyloxy-2-heptene 
• 114634-24-1 (2S,3S)-2-Phenyl-3-trimethylsilanyl-heptan-3-ol 
• 56844-77-0 2-Phenylheptan-3-ol 
• 56844-72-5 2-Phenylheptan-3-ol 

Relevant academic research and scientific papers

Direct Synthesis of Mono-α-arylated Ketones from Alcohols and Olefins via Ni-Catalyzed Oxidative Cross-Coupling

Controlled synthesis of α-monoarylated ketones is significant yet challenging due to the site-selectivity issues and nonproductive overarylation reactions. Herein, we reported the direct synthesis of α-arylated ketones enabled by Ni-catalyzed dehydrogenative cross-coupling reaction cascade between alcohols and olefins. The use of readily available and cost-effective alcohols and olefins provides a straightforward access to monoarylated ketones in good yields with exclusive selectivity without using any advanced synthetic intermediates.

Regioselective 1,2-Diol Rearrangement by Controlling the Loading of BF3·Et2O and Its Application to the Synthesis of Related Nor-Sesquiterene- and Sesquiterene-Type Marine Natural Products

The regiocontrolled rearrangement of 1,2-diols has been achieved by controlling the loading of BF3·Et2O. Its applicability is showcased by the divergent synthesis of austrodoral, austrodoric acid, and 8-epi-11-nordriman-9-one, as well as a formal synthesis of siphonodictyal B and liphagal. A new light is shed on piancol-type rearrangements that will be useful in diversity-oriented synthesis of related natural products.

Complementary catalytic strategies to access α-chiral aldehydes

The present article summarizes the development of two novel and complementary catalytic methods to access α-chiral aldehydes. A C1-symmetric chiral (P,N) ligand with a structure derived from the ubiquitous binepine scaffold has been specifically designed for the Pd-catalyzed α arylation of aldehydes to access indane derivatives with a well-defined quaternary stereocenter in high yields and excellent enantioselectivities. In addition, a dinuclear palladium hydride catalyst has been synthesized for the isomerization of terminal and trisubstituted epoxides into aldehydes and ketones respectively. Combined experimental and theoretical investigations pointed to an unprecedented 'epoxide-opening/hydride-transfer' sequence. The mechanism also features two distinct enantio-determining steps in the kinetic resolution of racemic epoxides. Schweizerische Chemische Gesellschaft.

Isomerization of terminal epoxides by a [Pd-H] catalyst: A combined experimental and theoretical mechanistic study

An unusual palladium hydride complex has been shown to be a competent catalyst in the isomerization of a variety of terminal and internal epoxides. The reaction displayed broad scope and synthetic utility. Experimental and theoretical evidence are provided for an unprecedented hydride mechanism characterized by two distinct enantio-determining steps. These results hold promise for the development of an enantioselective variant of the reaction.

Biocatalysed concurrent production of enantioenriched compounds through parallel interconnected kinetic asymmetric transformations

Parallel interconnected kinetic asymmetric transformations were performed in order to obtain enantioenriched derivatives starting from a set of racemic or prochiral compounds. Thus, in a one-pot reaction using two redox biocatalysts (a BVMO and an ADH) and a catalytic amount of cofactor that acts as a mediator, enantioenriched ketones, sulfoxides, and sec-alcohols were concurrently obtained in a strict parallel way, minimising the quantity of reagents employed. By selecting the appropriate biocatalysts, this methodology represents a potential tool for performing stereodivergent transformations.

One-carbon homologation of unsymmetrical ketones through magnesium β-oxido carbenoid rearrangement and trapping the enolate intermediates with electrophiles

A procedure for one-carbon homologation of unsymmetrical ketones, including one-carbon ring-expansion of 2-substituted cyclohexanones, through magnesium β-oxido carbenoid rearrangement as the key reaction is described. Addition of the α-sulfinyl carbanion of 1-chloroethyl p-tolyl sulfoxide to an unsymmetrical ketone gave two diastereomers as adducts in good yields. The adducts were treated with a base to give alkoxides, which were treated with a Grignard reagent to give magnesium β-oxido carbenoids. The β-oxido carbenoid rearrangement then took place to afford one-carbon homologated ketones having a methyl group at the α-position. Remarkable specificity or selectivity was observed in the rearrangement. The magnesium enolate intermediates of this reaction were found to be able to get trapped with several electrophiles to give one-carbon homologated α,α-disubstituted ketones. Origin of the specificity and selectivity is also discussed.

Titanocene(II)-promoted desulfurizative acylation of thioacetals with alkanenitriles

Ketones were obtained in good yields by titanocene(II)-promoted reaction of thioacetals with alkanenitriles. The regioselective formation of α-substituted ketone was observed when the reaction was carried out in the presence of methyl iodide or benzyl bro

The Chemistry of 5-Oxodihydroisoxazoles. XII. Trapping of Derived Ketenimines with Lithium Amides and Alkyllithiums

Isoxazolones unsubstituted at C 3 react with lithium amides or alkyllithiums to give ketenimines.The presence of an ethoxycarbonyl group at C 4 allows capture of this species by addition of a second equivalent of the lithiated species to give enolates which can be alkylated in situ.The presence of a phenyl group at C 4 gives a ketenimine which reacts intramolecularly in the presence of lithium amides, whereas alkyllithiums undergo addition in synthetically useful processes.

The Chemistry of 5-Oxodihydroisoxazoles. X. Butyllithium and Lithium Diisopropylamide Promoted Rearrangements of 3-Unsubstituted Isoxazol-5(2H)-ones

The reaction pathway of 3-unsubstituted isoxazol-5(2H)-ones with bases, proposed by Woodman to proceed via four intermediates to azetidine-2,4-diones, has been confirmed by the isolation of products unequivocally derived from each of the intermediates.Iso

Stereoselective Oxidation of β-Methyl-sec-alcohols and α-Methylketones by Corynebacterium equi IFO 3730

The enzyme system of Corynebacterium equi IFO 3730 catalyzed the diastereo-selective oxidation of β-methyl-sec-alcohols.For example, only the erythro isomer of 5-methyl-6-tetradecanol was oxidized to the corresponding ketone, the threo-alcohol remaining.M