Atroposelective Synthesis of Axially Chiral Styrenes by Platinum‐ Catalyzed Stereoselective Hydrosilylation of Internal Alkynes

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(30)

Опубликована: Май 25, 2023

Abstract Hydrofunctionalization of alkynes is one the most efficient ways to access axially chiral styrenes with open‐chained olefins. While great advances have been achieved for 1‐alkynylnaphthalen‐2‐ols and analogues, atroposelective hydrofunctionalization unactivated internal lags. Herein we reported a platinum‐catalyzed hydrosilylation first time. With monodentate TADDOL‐derived phosphonite L1 used as ligand, various were in excellent enantioselectivities high E ‐selectivities. Control experiments showed that N H‐arylamide groups significant effects on both yields could act directing groups. The potential utilities products shown by transformations amide motifs products.

Язык: Английский

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Cobalt‐Catalyzed Asymmetric Hydrogenation: Substrate Specificity and Mechanistic Variability

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(10)

Опубликована: Ноя. 28, 2023

Asymmetric hydrogenation finds widespread application in academia and industry. And indeed, a number of processes have been implemented for the production pharma agro intermediates as well flavors & fragrances. Although these are all based on use late transition metals catalysts, there is an increasing interest base metal catalysis view their lower cost expected different substrate scope. Catalysts cobalt already shown potential enantioselective chemistry. This review outlines impressive progress made recent years cobalt-catalyzed asymmetric unsaturated substrates. We also illustrate ligand dependent specificity mechanistic variability detail. may guide further catalyst development this research area.

Язык: Английский

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CoH-catalyzed asymmetric remote hydroalkylation of heterocyclic alkenes: a rapid approach to chiral five-membered S- and O-heterocycles

Chemical Science, Год журнала: 2024, Номер 15(23), С. 8888 - 8895

Опубликована: Янв. 1, 2024

A highly efficient method achieves precise construction of alkyl chiral centers at remote C3-positions in five-membered S/O-heterocycles via cobalt-catalyzed asymmetric hydroalkylation heterocyclic alkenes.

Язык: Английский

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Regio- and Enantioselective Hydromethylation of 3-Pyrrolines and Glycals Enabled by Cobalt Catalysis

JACS Au, Год журнала: 2024, Номер 4(6), С. 2312 - 2322

Опубликована: Июнь 11, 2024

Enantioenriched 3-methylpyrrolidine, with its unique chiral nitrogen-containing core skeleton, exists widely in various functional molecules, including natural products, bioactive compounds, and pharmaceuticals. Traditional methods for synthesizing these valuable methyl-substituted heterocycles often involve enzymatic processes or complex procedures auxiliaries, limiting the substrate scope efficiency. Efficient catalytic methylation, especially an enantioselective manner, has been a long-standing challenge chemical synthesis. Herein, we present novel approach remote stereoselective installation of methyl group onto N-heterocycles, leveraging CoH-catalyzed asymmetric hydromethylation strategy. By effectively combining commercial cobalt precursor modified bisoxazoline (BOX) ligand, variety easily accessible 3-pyrrolines can be converted to enantiopure 3-(isotopic labeling)methylpyrrolidine compounds outstanding enantioselectivity. This efficient protocol streamlines two-step synthesis enantioenriched which previously required up five six steps under harsh conditions expensive starting materials.

Язык: Английский

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Asymmetric hydrogenation of α-pyrrolyl terminal alkenes: an easy access to enantioenriched pyrroles bearing a C2 Me-substituted stereogenic center

Green Synthesis and Catalysis, Год журнала: 2025, Номер unknown

Опубликована: Апрель 1, 2025

Язык: Английский

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An Overview of Hydrogen Production from Renewable Sources and Its Main Applications

ChemistrySelect, Год журнала: 2024, Номер 9(35)

Опубликована: Сен. 12, 2024

Abstract There is a misconception that sustainability only related to greenhouse gas emissions into the atmosphere, and this risk which planet exposed. Sustainability multidimensional concept must advance simoutaneously on several fronts, such as urgent need increase energy, clean water, air, food, mobility, health, poverty reduction. All problems of these multi‐dimensions are aggravated by continuous growth world population, mainly in economic socio‐environmental issues. However, biggest challenge supply energy from renewable sources, all other dimensions depend policy decisions. The consumption fossil fuels has supplied current demand approximately 87 %. Still, there predictions depletion, effects caused environment production gases bring significant losses. In review, we will address most common methods for hydrogen production, well its main technological applications organic synthesis generation.

Язык: Английский

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Catalytic Hydrogenation of Terminal Alkenes by a (PPP) Pincer-Ligated Cobalt(II) Complex

Organometallics, Год журнала: 2023, Номер 42(13), С. 1439 - 1443

Опубликована: Май 23, 2023

A Co(II) complex, (PPHP)CoI2, was synthesized and evaluated as a precatalyst for the hydrogenation of terminal alkenes under mild conditions (1 atm H2, ambient temperature) using KBEt3H an activator. This catalytic system found to be active alkene substrates, including 1,1′-disubstituted alkenes, exhibit modest air moisture stability. preliminary investigation into substrate scope functional group tolerance performed. Upon completion reactions, sole metal complex observed identified dimeric species [(PPP)CoH]2 suggesting that catalytically may cobalt hydride monomer.

Язык: Английский

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Iridium-Catalyzed Asymmetric Transfer Hydrogenation of 1-Aryl-1-alkylethenes with Ethanol

Organic Letters, Год журнала: 2023, Номер 25(26), С. 4950 - 4954

Опубликована: Июнь 26, 2023

Asymmetric transfer hydrogenation of 1-aryl-1-alkylethenes with ethanol was developed a chiral (PCN)Ir complex as the precatalyst, featuring high enantioselectivities, good functional group tolerance, and operational simplicity. The method is further applied to formal intramolecular asymmetric alkenols without an external H-donor, producing tertiary stereocenter remote ketone simultaneously. utility catalytic system highlighted by gram scale synthesis key precursor (R)-xanthorrhizol.

Язык: Английский

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Enantioselective iron-catalysed transformations. An update

Tetrahedron, Год журнала: 2024, Номер 157, С. 133944 - 133944

Опубликована: Март 23, 2024

Язык: Английский

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Asymmetric hydrogenation of tetrasubstituted β-phosphorylated α,β-unsaturated esters catalyzed by nickel complexes of chiral phosphinooxazolines

Cell Reports Physical Science, Год журнала: 2024, Номер unknown, С. 102261 - 102261

Опубликована: Окт. 1, 2024

Язык: Английский

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