125653-66-9

Upstream product

• 38861-78-8 1-(4-isobutyl-phenyl)-ethanone 
• 108-05-4 vinyl acetate 
• 40150-92-3 1-(4-isobutylphenyl)ethanol 
• 63444-56-4 p-isobutylstyrene 
• 538-93-2 1-phenyl-2-methylpropane 
• 138948-58-0 (RS)-p-isobutyl-1-phenylethanol acetate 

Downstream Products

• 148366-87-4 ethyl (R)-4-[3-[4-[[1-(4-isobutylphenyl)ethyl]oxy]benzoyl]-1H-indol-1-yl]butyrate 

Relevant academic research and scientific papers

Enantiocomplementary decarboxylative hydroxylation combining photocatalysis and whole-cell biocatalysis in a one-pot cascade process

Designing a green, highly efficient and stereoselective catalytic system to generate valuable enantioenriched products is a long-standing goal in green chemistry. Here, we report a one-pot cascade combining photocatalysts with (R)- or (S)-selective ketoreductases for the decarboxylative carbonylation of carboxylic acids and the subsequent bioreduction to generate valuable chiral alcohols. Using this approach, various chiral alcohols with complementary (R)- or (S)-configurations were prepared with good yields (up to 93%) and excellent stereoselectivity (up to 99% ee). Such a photochemo-enzymatic one-pot whole-cell process combines the advantages of both photocatalysts and enzyme catalysts and provides a mild, green, metal-free and highly stereoselective alternative in asymmetric decarboxylative hydroxylation reactions.

Enantioselective reduction of aryl and hetero aryl methyl ketones using plant cell suspension cultures of Vigna radiata

Vigna radiata was investigated as whole cell catalyst for the bioreduction of aryl and heteroaryl prochiral ketones into optically active alcohols. The study indicates selective bioreduction of different substituted aryl and heteroaryl ketones (1a–12a) to their respective (S)–chiral alcohols (1b–12b) in good to high enantioselectivity (77.7–97.5%) with very good yields (73–82%). The results obtained confirm that the keto reductase has broad substrate specificity and selectivity in catalyzing both six and five-membered heteroaryl methyl ketones. The current methodology substantiates a promising and alternative green approach for the synthesis of secondary chiral alcohols of biological importance in a mild, cheap and environmentally benign process.

Semipermeable organic?inorganic hybrid microreactors for highly efficient and size-selective asymmetric catalysis

A highly efficient and size-selective organic?inorganic hybrid microreactor was fabricated successfully by assembling the semipermeable microporous silica hollow nanospheres at the interface of organic polymers containing an asymmetric transfer hydrogenation catalyst. The small micropores in the silica shells (1.0?1.5 nm) of the microreactors provide short mass-transfer channels for small molecules but prevent the diffusion of large reactants through the shell. At the same time, the combination of the outer microporous silica and inner polymers endows the microreactor with hydrophobic@ hydrophilic property, which helps its dispersion in water as well as the adsorption of reactant molecules from water, yielding an ideal microenvironment for water medium catalysis reactions. Such microreactors could efficiently catalyze the aqueous asymmetric transfer hydrogenation (ATH) of small-sized ketones with catalytic activity comparable to the homogeneous Rh-VBSDPEN catalyst (TOF 625 vs 724 h?1). Meanwhile, the microreactors also showed size selectivity toward large-sized reactants. Our studies provide an approach for the construction of artificial bioinspired microreactors with size-selective properties and favorable catalysis microenvironments.

Iron-catalyzed asymmetric hydrosilylation of ketones

A series of iron complexes of chiral iminopyridine-oxazoline (IPO) ligands have been synthesized. The most sterically hindered iron catalyst exhibits excellent activity (up to 99% yield) and high enantioselectivity (up to 93% ee) in asymmetric hydrosilylation of aryl ketones. This journal is

Catalytic asymmetric transfer hydrogenation of ketones using [Ru(p-cymene)Cl2]2 with chiral amino alcohol ligands

Catalytic asymmetric transfer hydrogenation of aromatic alkyl ketones has been investigated using [Ru(p-cymene)Cl2]2 and new derivatives of β-amino alcohols synthesized from (S)-(-)-lactic acid and mandelic acid as ligands. Chiral secondary alcohols were obtained with good to excellent conversion (60-90%) and moderate to good enantioselectivities (40-86%).

A remarkably effective catalyst for the asymmetric transfer hydrogenation of aromatic ketones in water and air

A Rh(III) complex generated in situ from [Cp*RhCl2] 2 and (1-R,2R)-N-(p-toluenesulfonyl)-1,2-cyclohexanediamine (TsCYDN) serves as a remarkably effective, robust catalyst for the asymmetric transfer hydrogenation of aromatic ketones by HCOONa in water in air, affording alcohols in up to 99% ee. The Royal Society of Chemistry 2005.

Enantioselective synthesis of (S)-α-arylpropionic acids via Pd-catalyzed kinetic resolution of benzylic alcohols

A convenient synthetic route for the synthesis of three (S)-α-propionic acids, (5)-naproxen (90% ee), (S)-ibuprofen (82% ee) and (5)-phenylpropionic acid (92% ee) is described. Pd-catalyzed oxidative kinetic resolution of the corresponding benzylic alcohols is used as a key step to introduce stereogenicity into the molecule.

4-(Benzoylindolizinyl)butyric acids; novel nonsteroidal inhibitors of steroid 5α-reductase. III

A novel series of indolizinebutyric acids with various benzoyl substituents was synthesized to develop nonsteroidal inhibitors of steroid 5α-reductase, and the structure-activity relationships in this series were studied. We previously reported the structure-activity relationships in a series of indolebutyric acids as well as the discovery of the novel nonsteroidal 5α-reductase inhibitor, FK143. We have now made other modifications to this compound to improve in vivo inhibitory activity. By altering the heterocyclic nucleus and changing the benzoyl substituent we have succeeded in identifying the strongly active compound, FK687, (S)-4-[1-[4-[[1-(4-isobutylphenyl)butyl]oxy]benzoyl]indolizin-3-yllbutyric acid, which displays strong in vitro inhibitory activity against the human enzyme and in vivo inhibitory activity against the castrated young rat model. This compound should be a useful agent for the treatment of benign prostatic hyperplasia.

Highly enantioselective aminoacylase-catalyzed transesterification of secondary alcohols

The aminoacylase (N-acyl-L-amino acid amidohydrolase; E.C. 3.5.1.14) from Aspergillus melleus, a readily available inexpensive enzyme, catalyzes the transesterification of a wide range of chiral secondary arylalkanols with essentially absolute stereoselectivity (E> 500). Moreover, the productivities obtained with 1-phenylethanol, 1-phenylpropanol, 1-(1-naphthyl)ethanol and 1- (2-naphthyl)ethanol were substantially higher than those in the corresponding lipase-catalyzed transesterifications. (C) 2000 Elsevier Science Ltd.

Catalytic Asymmetric Hydrocarboxylation and Hydrohydroxymethylation. A Two-Step Approach to the Enantioselective Functionalization of Vinylarenes

A method for the catalytic asymmetric hydrocarboxylation and hydrohydroxymethylation of vinylarenes is reported. By separating the step in which asymmetry is installed from the one where carbon-carbon bond formation takes place, a highly enantioselective and regioselective synthesis of Ibuprofen and its analogs is achieved. Stereochemistry is installed via an enantioselective hydroboration reaction, catalyzed by cationic rhodium BINAP complexes, and the homologation is carried out with halomethyllithium reagents. If CH2Cl2/n-BuLi is used as the homologating reagent, carboxylic acids are produced after oxidation. On the other hand, if CH2ClBr is used in combination with n-BuLi, the corresponding primary alcohol is produced. This latter transformation represents a previously unknown asymmetric hydrohydroxymethylation reaction. In both cases, complete retention of stereochemistry is observed, yielding products in up to 97% ee. Superior results are obtained if the initially formed catecholate is converted into a pinacolate prior to homologation.