152140-46-0

Upstream product

• 20859-19-2 (+/-)-trans-2-(4-methoxyphenyl)cyclohexanol 
• 108-24-7 acetic anhydride 
• 7150-18-7 3β-acetoxyetienic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 286-20-4 cyclohexane-1,2-epoxide 
• 1373216-32-0 tris(4-isopropylphenyl)silyl chloride 
• 37087-68-6 2-(4-methoxyphenyl)cyclohexanone 
• 13139-86-1 4-methoxyphenyl magnesium bromide 

Relevant academic research and scientific papers

A new nucleophilic catalyst for kinetic resolution of racemic sec-alcohols

A new tertiary amine-based nucleophilic catalyst, derived from a simple combination of commercially available compounds, affords good to excellent kinetic resolution of racemic sec-alcohols.

Synthesis method of chiral trans-2-substituted naphthenic alcohol

The invention relates to a synthesis method of chiral trans-2-substituted naphthenic alcohol. The invention provides a method for synthesizing chiral trans-cycloalkanol through asymmetric hydrogenation of palladium-catalyzed 2-substituted cyclic ketone. According to the method,a chiral diphosphine P-P * complex of metal palladium is taken as a catalyst, an acid additive is used in cooperation, asymmetric hydrogenation is carried out on a 2-substituted cyclic ketone compound to obtain a corresponding chiral trans-cycloalkanol compound. the enantiomeric excess of the chiral trans-cycloalkanol compound can reach 97% at most, and the trans-selectivity of the chiral trans-cycloalkanol compound is up to 20: 1. The method is simple and convenient to operate, practical, easy to implement, high in yield, high in atom economy and environment-friendly; the catalyst is commercially available; the reaction conditions are mild; and the method has a potential practical application value.

Palladium-catalyzed asymmetric hydrogenation of 2-aryl cyclic ketones for the synthesis oftranscycloalkanols through dynamic kinetic resolution under acidic conditions

The first efficient palladium-catalyzed asymmetric hydrogenation of 2-aryl cyclic ketones has been described through dynamic kinetic resolution under acidic conditions, providing a facile access to chiraltranscycloalkanol derivatives with excellent enantioselectivities.

Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Br?nsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions

An enantioselective catalytic inverse-electron-demand Diels-Alder reaction of salicylaldehyde acetal-derived oxocarbenium ions and vinyl ethers to generate 2,4-dioxychromanes is described. Chiral pentacarboxycyclopentadiene (PCCP) acids are found to be effective for a variety of substrates. Computational and X-ray crystallographic analyses support the unique hypothesis that an anion with point-chirality-induced helical chirality dictates the absolute sense of stereochemistry in this reaction.

Diastereoselective and Enantioselective Silylation of 2-Arylcyclohexanols

The silylation-based kinetic resolution of trans 2-arylcyclohexanols was accomplished by employing a triaryl silyl chloride as the derivatizing reagent with a commercially available isothiourea catalyst. The methodology is selective for the trans diastereomer over the cis, which provides an opportunity to selectively derivatize one stereoisomer out of a mixture of four. By employing this technology, a facile, convenient method to form a highly enantiomerically enriched silylated alcohol was accomplished through a one-pot reduction-silylation sequence that started with a 2-aryl-substituted ketone.

Enantioselective cross-coupling of meso -epoxides with aryl halides

The first enantioselective cross-electrophile coupling of aryl bromides with meso-epoxides to form trans-β-arylcycloalkanols is presented. The reaction is catalyzed by a combination of (bpy)NiCl2 and a chiral titanocene under reducing conditions. Yields range from 57 to 99% with 78-95% enantiomeric excess. The 30 examples include a variety of functional groups (ether, ester, ketone, nitrile, ketal, trifluoromethyl, sulfonamide, sulfonate ester), both aryl and vinyl halides, and five- to seven-membered rings. The intermediacy of a carbon radical is strongly suggested by the conversion of cyclooctene monoxide to an aryl [3.3.0]bicyclooctanol.

A nonenzymatic kinetic resolution of (±)-trans-2-arylcyclohexanols via esterification using polymer-supported DCC, DMAP, and 3 β- acetoxyetienic acid

A nonenzymatic kinetic resolution of (±)-trans-2-arylcyclohexanols was carried out by esterification using polymer-supported N,N′- dicyclohexylcarbodiimide (DCC), dimethylaminopyridine (DMAP), and 3β-acetoxyetienic acid. The efficiency of the kinetic resolution was comparable to the enzymatic method when arylcyclohexanols bearing a condensed-aromatic ring were used. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communication to view the free supplemental file.

Synthesis of an enantiopure 2-arylcyclohexanols from prochiral enol acetates by an enantioselective protonation/diastereoselective reduction sequence

The enantioselective protonation with 2-sulfinyl alcohols of lithium enolates of 2-arylcyclohexanones with different substituents on the phenyl group takes place with excellent enantioselectivities (89-99%). Chiral 2-phenylcyclohexanone and 2-arylcyclohexanones carrying electron donor substituents on the aromatic ring are converted into the corresponding trans-2-arylcyclohexanols by diastereoselective reduction with sodium naphthalenide in the presence of acetamide. The stereochemical integrity of the tertiary stereocenter is fully preserved using this reduction procedure. Interestingly, the chiral proton source is not consumed in the synthesis.

Effective nonenzymatic kinetic resolution of (±)-trans-2-arylcyclohexanols using 3β-acetoxyetienic acid, DCC, and DMAP

(1R,2S)-trans-2-Arylcyclohexanols of high enantiomerically purity were obtained by the simple stirring of the corresponding (±)-arylcyclohexanols with 3β-acetoxyetienic acid, DCC, and DMAP at room temperature.

1H NMR determination of absolute configuration of 1- or 2-aryl-substituted alcohols and amines by means of their diastereomers: Novel separation technique of diastereomeric derivatives of pyridyl alcohols by extraction

Abstract: A convenient method to determine the absolute configuration of trans-2-aryl cyclohexanols, 1-aryl alcohols and amines was achieved. This method takes advantage of the 1H NMR spectroscopic observations of the remarkable high-field shift of C18-CH3 protons caused by the aromatic shielding effect. It is based on a discrimination of the difference of the environments in two diastereomers derived from 3β-acetoxy-5-etienic acid. Furthermore, it was observed that the corresponding diastereomeric derivatives of the pyridyl alcohols were simply separated by extraction based on the difference in their basicity.