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General Description

(S)-1-(p-biphenyl)ethanol is a chemical compound with the molecular formula C14H14O. It is a chiral compound with two enantiomers, (R)- and (S)-1-(p-biphenyl)ethanol. (S)-1-(p-biphenyl)ethanol is used in various medicinal and industrial applications, particularly as a chiral building block in the synthesis of pharmaceuticals and agrochemicals. It has also been studied for its potential anti-inflammatory and antimicrobial properties. (S)-1-(p-biphenyl)ethanol is a colorless to pale yellow liquid at room temperature and is soluble in organic solvents such as ethanol and acetone.

Upstream product

• 2350-89-2 p-vinylbiphenyl 
• 92-91-1 biphenyl-4-acetaldehyde 
• 108-05-4 vinyl acetate 
• 544-97-8 dimethyl zinc(II) 
• 3218-36-8 4-Phenylbenzaldehyde 
• 108-86-1 bromobenzene 
• 1173922-36-5 (S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanol 
• 104013-25-4 S-p-iodo-α-methylbenzyl alcohol 
• 98-80-6 phenylboronic acid 
• 13329-40-3 4-Iodoacetophenone 
• 3562-73-0 1-(4-phenyl-phenyl)-1-ethanol 
• 5707-44-8 4-ethylbiphenyl 
• 99-90-1 para-bromoacetophenone 
• 99-91-2 para-chloroacetophenone 

Relevant academic research and scientific papers

An integrated immobilization strategy manipulates dual active centers to boost enantioselective tandem reactions

Manipulation of dual active centers via an integrated immobilization strategy can overcome the restriction of homogeneous catalysis in a sequential organic transformation. Herein, by utilizing hollow-shell-structured silica, hydrogen-bonding immobilization via a ship-in-a-bottle synthesis locks a Pd(carbene) center in a nanocage and covalent-bonding immobilization tethers chiral Ru(diamine) centers within the nanochannels, constructing a hetero-bifunctional catalyst. The benefit of this dual center manipulation enables a challenging Suzuki coupling-asymmetric transfer hydrogenation tandem reaction, and the advantage of this process provides various chiral biarylols with enhanced reactivity and enantioselectivity.

Combination of a Suzuki cross-coupling reaction using a water-soluble palladium catalyst with an asymmetric enzymatic reduction towards a one-pot process in aqueous medium at room temperature

We report the combination of a palladium-catalyzed Suzuki cross-coupling reaction with an enzymatic reduction in a one-pot process in aqueous medium, in which both reaction steps are conducted at room temperature. By using a water-soluble palladium catalyst system, which is prepared from commercially available palladium chloride and TPPTS (tris(3-sulfonatophenyl)phosphine hydrate, sodium salt), the palladium-catalyzed step runs at room temperature in a mixture of isopropanol and water. After adjusting the pH value to pH 7, the resulting biaryl ketone is then directly reduced in situ via an enzymatic asymmetric reduction in the presence of an alcohol dehydrogenase (ADH), leading to the desired alcohol with up to >95% conversion (over two steps) and excellent enantioselectivities of >99% ee. Notably, both enantiomers of the desired alcohol are accessible depending on the source of applied ADH.

Borohydride intermediates pave the way for magnesium-catalysed enantioselective ketone reduction

A magnesium precatalyst for the highly enantioselective hydro-boration of CO bonds is reported. The mechanistic basis of the unprecedented selectivity of this transformation has been investi-gated experimentally by isolation of catalytic intermediates and theoretically by DFT calculations. The facile formation of a magnesium borohydride species is critical in overcoming competing pathways in the selectivity-determining insertion step.

Cyclodextrin-[RuCl2(Arene)]2 conjugates: Another way to enhance the enantioselectivity of aromatic ketones reduction by aromatic ligands' volume

Eight amino alcohol-modified β-CDs CD-1-CD-8 have been synthesized in acceptable yields and were employed to form artificial metalloenzymes with [RuCl2(Benzene)]2 and [RuCl2(Mesitylene)] 2, respectively. All the conformations of CD-1-CD-8, the complexes between CD-1-CD-8 and [RuCl2(Arene)]2, and the inclusion complexes between CD-1-CD-8 and acetophenone were characterized by UV, 1H NMR, 1H ROESY NMR, and quantum calculation. The catalytic activity of the formed artificial metalloenzymes in the asymmetric hydrogenation of aromatic ketones, especially the effect of the aromatic ligands' volume on the enantioselectivity were investigated in detail, in which it was obvious that the enantioselectivity increased as the increase in the aromatic ligands' volume. For the best artificial metalloenzyme constructed from the complex between CD-8 and [RuCl2(Mesitylene)]2, which not only exhibits a good tolerance to a wide range of substrates but also demonstrates some substrate selectivity, 76.39% ee was obtained for acetophenone and 79.67% ee for 2-acetylnaphthalene. A strategy to improve the enantioselectivity in the asymmetric reactions catalyzed by the artificial metalloenzymes based on CDs has been provided.

Facile assembly of bifunctional, magnetically retrievable mesoporous silica for enantioselective cascade reactions

An integrated immobilization to encapsulate the Pd/C-coated magnetic nanoparticles within the chiral Ru/diamine-functionalized silica shell for the construction of a bifunctional magnetic catalyst is developed. This catalyst realizes a synergistic Suzuki cross-coupling/asymmetric transfer hydrogenation and a successive reduction/asymmetric transfer hydrogenation for the preparation of chiral aromatic alcohols.

Identification and development of biphenyl substituted iminosugars as improved dual glucosylceramide synthase/neutral glucosylceramidase inhibitors

This work details the evaluation of a number of N-alkylated deoxynojirimycin derivatives on their merits as dual glucosylceramide synthase/neutral glucosylceramidase inhibitors. Building on our previous work, we synthesized a series of d-gluco and l-ido-configured iminosugars N-modified with a variety of hydrophobic functional groups. We found that iminosugars featuring N-pentyloxymethylaryl substituents are considerably more potent inhibitors of glucosylceramide synthase than their aliphatic counterparts. In a next optimization round, we explored a series of biphenyl-substituted iminosugars of both configurations (d-gluco and l-ido) with the aim to introduce structural features known to confer metabolic stability to drug-like molecules. From these series, two sets of molecules emerge as lead series for further profiling. Biphenyl-substituted l-ido-configured deoxynojirimycin derivatives are selective for glucosylceramidase and the nonlysosomal glucosylceramidase, and we consider these as leads for the treatment of neuropathological lysosomal storage disorders. Their d-gluco-counterparts are also potent inhibitors of intestinal glycosidases, and because of this characteristic, we regard these as the prime candidates for type 2 diabetes therapeutics.

Novel Insights into the Combination of Metal- and Biocatalysis: Cascade One-Pot Synthesis of Enantiomerically Pure Biaryl Alcohols in Deep Eutectic Solvents

One of the pioneering examples of chemoenzymatic cascades in water such as the palladium-catalysed Suzuki-cross coupling followed by an enzymatic reduction has been revisited by the employment of a medium containing Deep Eutectic Solvents (DESs) for the catalytic performance. Thus, the unique properties of these neoteric solvents enabled to reach high substrate concentration for the overall process. Moreover, both isolated enzymes and whole cells exhibited excellent activities which allowed to obtain a set of chiral biaryl alcohols in good yields and very high enantiomeric excess (>99 %).

Real-Time Control of the Enantioselectivity of a Supramolecular Catalyst Allows Selecting the Configuration of Consecutively Formed Stereogenic Centers

The enantiomeric state of a supramolecular copper catalyst can be switched in situ in ca. five seconds. The dynamic property of the catalyst is provided by the non-covalent nature of the helical assemblies supporting the copper centers. These assemblies are formed by mixing an achiral benzene-1,3,5-tricarboxamide (BTA) phosphine ligand (for copper coordination) and both enantiomers of a chiral phosphine-free BTA co-monomer (for chirality amplification). The enantioselectivity of the hydrosilylation reaction is fixed by the BTA enantiomer in excess, which can be altered by simple BTA addition. As a result of the complete and fast stereochemical switch, any combination of the enantiomers was obtained during the conversion of a mixture of two substrates.

Multiple Functionalized Hyperbranched Polyethoxysiloxane Promotes Suzuki Coupling Asymmetric Transfer Hydrogenation One-Pot Enantioselective Organic Transformations

Utilization of amphiphilic poly(ethylene glycol) monomethyl ether modified hyperbranched polyethoxysiloxane as a support for the construction of bifunctional heterogeneous catalysts enables a highly efficient catalytic system thanks to its amphiphilic nature in aqueous organic transformations. Herein, through a three-component self-assembly procedure, we incorporate palladium/phosphine and chiral ruthenium/diamine functionality within poly(ethylene glycol) monomethyl ether modified hyperbranched polyethoxysiloxane, fabricating a multiple functionalized polyethoxysiloxane based mesoporous material. Structural analyses and characterizations disclose that well-defined dual single-site active centers are distributed uniformly within monodisperse mesoporous silica nanoparticles. As a bifunctional heterogeneous catalyst, this material performs the one-pot enantioselective tandem reaction of Pd-catalyzed Suzuki cross-coupling and Ru-catalyzed asymmetric transfer hydrogenation, affording various chiral biaryl alcohols with high yields and up to 99 % enantioselectivity. Furthermore, the catalyst can be recovered and recycled eight times without loss of its catalytic activity, demonstrating the practicability of the preparation of optically pure biaryl alcohols in one-pot organic transformation.

A chiral iron complex containing a bis(oxazolinyl)phenyl ligand: Preparation and asymmetric hydrosilylation of ketones

New chiral pincer iron complexes having bis(oxazolinyl)phenyl ligands have been synthesized by oxidative addition of Fe2(CO)9 to 2-bromo-substituted ligands. This chiral pincer iron complex can catalyze the asymmetric hydrosilylation of simple aromatic ketones to give the corresponding alcohols.