Rhodium-Catalyzed Asymmetric C–H Functionalization Reactions

Chemical Reviews, Год журнала: 2023, Номер 123(16), С. 10079 - 10134

Опубликована: Авг. 1, 2023

This review summarizes the advancements in rhodium-catalyzed asymmetric C–H functionalization reactions during last two decades. Parallel to rapidly developed palladium catalysis, rhodium catalysis has attracted extensive attention because of its unique reactivity and selectivity reactions. In recent years, Rh-catalyzed have been significantly many respects, including catalyst design, reaction development, mechanistic investigation, application synthesis complex functional molecules. presents an explicit outline catalysts ligands, mechanism, scope coupling reagents, applications.

Язык: Английский

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Catalytic Asymmetric Synthesis of Atropisomers Bearing Multiple Chiral Elements: An Emerging Field

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(3)

Опубликована: Ноя. 2, 2023

With the rapid development of asymmetric catalysis, demand for enantioselective synthesis complex and diverse molecules with different chiral elements is increasing. Owing to unique features atropisomerism, catalytic atropisomers has attracted a considerable interest from chemical science community. In particular, introducing additional elements, such as carbon centered chirality, heteroatomic planar helical into provides an opportunity incorporate new properties axially compounds, thus expanding potential applications atropisomers. Thus, it important perform transformations synthesize bearing multiple elements. spite challenges in transformations, recent years, chemists have devised powerful strategies under organocatalysis or metal synthesizing wide range enantioenriched Therefore, become emerging field. This review summarizes progress this field indicates challenges, thereby promoting horizon.

Язык: Английский

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Atroposelective catalysis

Nature Reviews Chemistry, Год журнала: 2024, Номер 8(7), С. 497 - 517

Опубликована: Июнь 18, 2024

Язык: Английский

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Synthesis of Axially Chiral Biaryls through Cobalt(II)‐Catalyzed Atroposelective C−H Arylation

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(40)

Опубликована: Авг. 16, 2023

Highly efficient synthesis of axially chiral biaryl amines through cobalt-catalyzed atroposelective C-H arylation using easily accessible cobalt(II) salt and salicyloxazoline ligand has been reported. This methodology provides a straightforward sustainable access to broad range enantioenriched biaryl-2-amines in good yields (up 99 %) with excellent enantioselectivities % ee). The synthetic utility the unprecedented method is highlighted by its scalability diverse transformations.

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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Synthesis of Alkene Atropisomers with Multiple Stereogenic Elements via Catalytic Asymmetric Rearrangement of 3‐Indolylmethanols

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Июль 23, 2024

Abstract Catalytic enantioselective preparation of alkene atropisomers with multiple stereogenic elements and discovery their applications have become significant but challenging issues in the scientific community due to unique structures this class atropisomers. We herein report first catalytic atroposelective cyclopentenyl[ b ]indoles, a new kind atropisomers, point axial chirality via an unusual rearrangement reaction 3‐indolylmethanols under asymmetric organocatalysis. Notably, novel type promising developing chiral ligands or organocatalysts, discovering antitumor drug candidates fluorescence imaging materials. Moreover, theoretical calculations elucidated possible mechanism non‐covalent interactions control enantioselectivity. This approach offers synthetic strategy for elements, represents 3‐indolylmethanols, which will advance chemistry indole chemistry.

Язык: Английский

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Rhodium-catalyzed atroposelective access to trisubstituted olefinsviaC–H bond olefination of diverse arenes

Chemical Science, Год журнала: 2023, Номер 14(29), С. 7999 - 8005

Опубликована: Янв. 1, 2023

The atroposelective synthesis of axially chiral acyclic olefins remains a daunting challenge due to their relatively lower racemization barriers, especially for trisubstituted ones. In this work, C-H olefination has been realized open-chain via activation two classes (hetero)arenes in the coupling with sterically hindered alkynes. employment phenyl N-methoxycarbamates as arene reagents afforded phenol-tethered olefins, carbamate being traceless directing group. N-methoxy-2-indolylcarboxamides corresponding olefin by circumventing redox-neutral [4 + 2] annulation. reactions proceeded excellent Z/E selectivity, chemoselectivity, regioselectivity, and enantioselectivity both hydroarylation systems.

Язык: Английский

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Axially chiral styrene-based organocatalysts and their application in asymmetric cascade Michael/cyclization reaction

Chemical Science, Год журнала: 2023, Номер 14(35), С. 9496 - 9502

Опубликована: Янв. 1, 2023

An axially chiral styrene-based organocatalyst, featuring a combination of structure and pyrrole ring, has been designed synthesized. This catalyst demonstrates remarkable capabilities in producing wide range densely substituted spirooxindoles that feature an alkyne-substituted quaternary stereogenic center. These are generated through mild cascade Michael/cyclization reactions, resulting high conversion rates exceptional enantioselectivity. Our catalytic model, based on experiments, X-ray analysis DFT calculations suggests matched π-π interactions multiple H-bonds between the organocatalyst substrates play significant roles controlling stereoselectivity reaction.

Язык: Английский

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Catalytic Synthesis of β‐(Hetero)arylethylamines: Modern Strategies and Advances

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(41)

Опубликована: Авг. 21, 2023

Abstract β‐(Hetero)arylethylamines appear in a myriad of pharmaceuticals due to their broad spectrum biological properties, making them prime candidates for drug discovery. Conventional methods preparation often require engineered substrates that limit the flexibility synthetic routes and diversity compounds can be accessed. Consequently, provide rapid versatile access those scaffolds remain limited. To overcome these challenges, chemists have designed innovative modular strategies β‐(hetero)arylethylamine motif, paving way more extensive use future pharmaceuticals. This review outlines recent progresses synthesis (hetero)arylethylamines emphasizes how innovations enabled new levels molecular complexity, selectivity, practicality.

Язык: Английский

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Catalytic stereodivergent and simultaneous construction of axial and point chirality

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(12), С. 3308 - 3319

Опубликована: Янв. 1, 2024

An unprecedented ligand-enabled stereodivergent construction of both N–N axial and point chirality in a single step is reported.

Язык: Английский

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