Dynamic Kinetic Reductive Grignard-Type Addition for the Construction of Axial and Central Chirality

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 1147 - 1157

Опубликована: Янв. 3, 2025

This study describes a photoredox/cobalt dual-catalyzed asymmetric Grignard-type addition reaction, enabling the synthesis of axially chiral hexatomic (six–six) N-heterobiaryls bearing extra secondary alcohol unit via an efficient dynamic kinetic transformation racemic N-heterobiaryl triflate substrates. The conversion facilitated both photoredox and classical reductive reaction conditions exhibits good functional group tolerance, broad substrate scope, satisfactory stereoselectivity. Furthermore, control experiments density theory calculations provide preliminary mechanistic insights.

Язык: Английский

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Rhodium-Catalyzed Atroposelective C–H Alkylation of 1-Aryl Isoquinoline Derivatives with Cyclopropanols

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 4017 - 4024

Опубликована: Фев. 20, 2025

Язык: Английский

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Enantioselective synthesis of molecules with multiple stereogenic elements

Chemical Society Reviews, Год журнала: 2024, Номер 53(22), С. 11165 - 11206

Опубликована: Янв. 1, 2024

This review explores the fascinating world of molecules featuring multiple stereogenic elements, unraveling different strategies designed over years for their enantioselective synthesis.

Язык: Английский

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Access to distal biaxial atropisomers by iridium catalyzed asymmetric C–H alkylation

Chemical Science, Год журнала: 2024, Номер 15(33), С. 13541 - 13549

Опубликована: Янв. 1, 2024

Herein, we report an iridium-catalyzed asymmetric C–H activation combined with a desymmetrization strategy for synthesizing distal biaxial atropisomers excellent stereoselectivity, displaying promising photophysical and chiroptical properties.

Язык: Английский

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An Aza-Enolate Strategy Enables Iridium-Catalyzed Enantioselective Hydroalkenylations of Minimally Polarized Alkenes en Route to Complex N-Aryl β²-Amino Acids

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(33), С. 22923 - 22929

Опубликована: Авг. 6, 2024

Cationic Ir(I)-complexes modified with homochiral diphosphines promote the hydroalkenylative cross-coupling of β-(arylamino)acrylates monosubstituted styrenes and α-olefins. The processes are dependent on presence an NH unit, it is postulated that metalation this generates iridium aza-enolate engages alkene during C-C bond forming event. method offers high branched selectivity enantioselectivity occurs complete atom economy. Diastereocontrolled reduction products provides β

Язык: Английский

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The influence of acid additive on linear and branch selectivity in the C−H alkylation of the N-pyridinecarbonyl protected 2-methylbenzylamine with 1-heptene catalyzed by Rh2(OAc)4: a theoretical investigation

Organic Chemistry Frontiers, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

The role of an acid additive and the origins reaction are clarified through our calculations.

Язык: Английский

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Modular Assembly of Axially Chiral QUINAP Derivatives via Nickel-Catalyzed Enantioselective C–P Cross-Coupling

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 8268 - 8273

Опубликована: Май 2, 2025

Язык: Английский

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Ir-Catalyzed Regio- and Enantioselective C–H Addition to 1,1-Disubstituted Alkenes Enabled by the Directing Group: Construction of Acyclic Quaternary Stereocenters

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 8733 - 8739

Опубликована: Май 8, 2025

Язык: Английский

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Iridium-Catalyzed Asymmetric Hydroarylation of Unactivated Alkenes with Heterobiaryls: Simultaneous Construction of Axial and Central Chirality

Organic Letters, Год журнала: 2024, Номер 26(32), С. 6835 - 6840

Опубликована: Авг. 7, 2024

There are only a few examples being reported for the simultaneous control of central chirality and axial because it is more challenging. Herein, we report an iridium-catalyzed asymmetric hydroarylation unactivated alkenes with heterobiaryls to simultaneously construct chirality. The reaction showed broad substrate scope delivered products satisfactory results. results experiments demonstrated that FerroLANE ligand promotes proceed along specific modified Chalk-Harrod mechanism.

Язык: Английский

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Diastereodivergent Parallel Kinetic Resolution of Racemic 2-Substituted Pyrrolidines via Iridium-Catalyzed C(sp³)–H Borylation

ACS Catalysis, Год журнала: 2024, Номер unknown, С. 18701 - 18707

Опубликована: Дек. 8, 2024

Chiral 2,5-disubstituted pyrrolidines are ubiquitous subunits in natural products, bioactive compounds, pharmaceuticals, and chiral catalysts. However, their asymmetric synthesis still presents a formidable challenge. We herein report rare example of diastereodivergent parallel kinetic resolution racemic 2-substituted via C(sp3)–H borylation. A vast array enantioenriched cis- trans-2,5-disubstituted were obtained with high enantioselectivities. The synthetic utility was demonstrated by downstream transformations, including the optically active pyrrolidine 197B cis-pyrrolidine 225H.

Язык: Английский

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