Atroposelective Synthesis of Axially Chiral Diaryl Ethers by N-Heterocyclic-Carbene-Catalyzed Sequentially Desymmetric/Kinetic Resolution Process

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(6), С. 4067 - 4073

Опубликована: Фев. 23, 2024

We describe herein an N-heterocyclic-carbene-catalyzed atroposelective synthesis of axially chiral diaryl ethers. Through a sequentially enantioselective desymmetric process and kinetic resolution process, the products could be constructed in good yields with excellent enantiopurities. Both alcohols phenols were compatible this catalytic system. The carboxylic acids derived from esters proven to potential ligands for asymmetric synthesis, example, Rh(III)-catalyzed C–H functionalization.

Язык: Английский

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Axial Chirality in Alkylidene‐Cyclic Molecules

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(20)

Опубликована: Март 30, 2023

Abstract Axial chirality is an interesting stereoisomeric phenomenon in organic chemistry and a key structural feature of several compounds. Atropisomers such as biaryls, anilides diaryl ethers are one type axially chiral compounds, whose axial resulted from rotationally blocked single bond. Allenes, spiranes alkylidenecycloalkanes another compounds their come the perpendicular geometry two pairs substituents. The atropisomers, allenes has been widely investigated well developed, while similar alkylidene‐cyclic molecules gained very limited attentions. This concept focuses on summarizing recent advances arouses research interests to this promising field.

Язык: Английский

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Asymmetric Synthesis of Axially Chiral Molecules via Organocatalytic Cycloaddition and Cyclization Reactions

Molecules, Год журнала: 2023, Номер 28(11), С. 4306 - 4306

Опубликована: Май 24, 2023

Atropisomeric molecules are present in many natural products, biologically active compounds, chiral ligands and catalysts. Many elegant methodologies have been developed to access axially molecules. Among them, organocatalytic cycloaddition cyclization attracted much attention because they widely used the asymmetric synthesis of biaryl/heterobiaryls atropisomers via construction carbo- hetero-cycles. This strategy has undoubtedly become will continue be a hot topic field catalysis. review aims highlight recent advancements this atropisomer by using different organocatalysts strategies. The each atropisomer, its possible mechanism, role catalysts, potential applications illustrated.

Язык: Английский

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Bioactive atropisomers: Unraveling design strategies and synthetic routes for drug discovery

Medicinal Research Reviews, Год журнала: 2024, Номер 44(5), С. 1971 - 2014

Опубликована: Март 21, 2024

Atropisomerism, an expression of axial chirality caused by limited bond rotation, is a prominent aspect within the field medicinal chemistry. It has been shown that atropisomers wide range compounds, including established FDA-approved drugs and experimental molecules, display markedly different biological activities. The time-dependent reversal in poses complexity obstacles process drug discovery development. Nonetheless, recent progress understanding atropisomerism enhanced characterization methods have greatly assisted chemists effective development atropisomeric molecules. This article provides comprehensive review their special design thoughts, synthetic routes, activities, serving as reference for synthesis evaluation bioactive future.

Язык: Английский

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A concise asymmetric total synthesis of 18-Ar-spirotryprostatin A analogs

Tetrahedron Letters, Год журнала: 2024, Номер 138, С. 154968 - 154968

Опубликована: Фев. 21, 2024

Язык: Английский

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