The Proton of Alcohols as Hydrogen Source in Diboron-Mediated Nickel-Catalyzed Asymmetric Transfer Hydrogenation of Cyclic N-Sulfonyl Imines

The Journal of Organic Chemistry, Год журнала: 2023, Номер 89(1), С. 710 - 718

Опубликована: Дек. 15, 2023

The proton of alcohols as the sole hydrogen source in diboron-mediated nickel-catalyzed asymmetric transfer hydrogenation cyclic N-sulfonyl imines has been developed, providing chiral sulfamidates excellent enantioselectivities. mechanistic investigations suggested that could be activated by tetrahydroxydiboron to form active nickel hydride species.

Язык: Английский

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A versatile cobalt catalyst for highly enantioselective hydrogenation of carbonyl compounds

Chem Catalysis, Год журнала: 2024, Номер 4(5), С. 100999 - 100999

Опубликована: Май 1, 2024

Язык: Английский

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Enantioselective Synthesis of Chiral β²-Amino Phosphorus Derivatives via Nickel-Catalyzed Asymmetric Hydrogenation

Journal of the American Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Дек. 27, 2024

Compared with chiral β3-amino phosphorus compounds, which can be easily derived from natural optically pure α-amino acids, obtaining β2-amino derivatives remains a challenge. These derivatives, cannot amino possess unique biological activities or potential catalytic activities. Herein, highly enantioselective hydrogenation for the preparation of E-β-enamido compounds is reported by using green and low-cost earth-abundant metal nickel catalyst (13 examples 99% ee). In particular, this system provides same enantiomer product E- Z-alkene substrates, E/Z-substrate mixtures provide good results (up to 96% The products diversely derivatized, exhibit as novel β2-aminophosphine ligands. Density functional theory calculations reveal that weak attractive interactions between substrate are crucial achieving perfect enantioselectivities. addition, different coordination modes Z-substrates may result in formation product.

Язык: Английский

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Chemoenzymatic approach towards the synthesis of the antitumor and antileishmanial marine metabolite (+)-Harzialactone A via the stereoselective, biocatalyzed reduction of a prochiral ketone

Bioorganic Chemistry, Год журнала: 2023, Номер 138, С. 106675 - 106675

Опубликована: Июнь 10, 2023

As a rich source of biological active compounds, marine natural products have been increasingly screened as candidates for developing new drugs. Among the several and metabolites, (+)-Harzialactone A has drawn considerable attention its antitumor antileishmanial activity. In this work chemoenzymatic approach implemented preparation metabolite A. The synthesis involved stereoselective, biocatalyzed reduction prochiral ketone 4-oxo-5-phenylpentanoic acid or corresponding esters, all generated by chemical reactions. collection different promiscuous oxidoreductases (both wild-type engineered) diverse microorganism strains were investigated to mediate bioconversions. After co-solvent co-substrate investigation in order enhance bioreduction performance, T. molischiana presence NADES (choline hydrochloride-glucose) ADH442 identified most promising biocatalysts, allowing obtainment (S)-enantiomer with excellent ee (97% > 99% respectively) good conversion (88% 80% respectively). successful attempt study provides

Язык: Английский

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Dynamic kinetic resolution of α-F-β-ketone amides (esters) via Ir/f-diaphos-catalyzed asymmetric hydrogenation

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(8), С. 2201 - 2207

Опубликована: Янв. 1, 2024

Highly reactive and highly stereoselective asymmetric hydrogenation of α-F-β-ketone amides (esters) via Ir/f-diaphos-catalyzed dynamic kinetic resolution is reported.

Язык: Английский

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