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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Recent advances in organocatalytic atroposelective reactions

Beilstein Journal of Organic Chemistry, Год журнала: 2025, Номер 21, С. 55 - 121

Опубликована: Янв. 9, 2025

Axial chirality is present in a variety of naturally occurring compounds, and becoming increasingly relevant also medicine. Many axially chiral compounds are important as catalysts asymmetric catalysis or have chiroptical properties. This review overviews recent progress the synthesis via organocatalysis. Atroposelective organocatalytic reactions discussed according to dominant catalyst activation mode. For covalent organocatalysis, typical enamine iminium modes presented, followed by N -heterocyclic carbene-catalyzed reactions. The bulk devoted non-covalent activation, where Brønsted acids feature most prolific catalytic structure. last part article discusses hydrogen-bond-donating other motifs such phase-transfer catalysts.

Язык: Английский

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Asymmetric construction of axial and planar chirality with N-heterocyclic carbene (NHC) organocatalysis

Science China Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 30, 2024

Язык: Английский

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Carbenoid Reactions Promoted by Solids: From Lewis to Brønsted Catalysts

Accounts of Chemical Research, Год журнала: 2025, Номер unknown

Опубликована: Апрель 23, 2025

ConspectusDiazocarbonyl compounds have become essential tools in organic synthesis, due to their ability situ generate reactive carbenes and be inserted a variety of otherwise stable bonds, such as C-H, C-C, H-O, so on. However, soluble metal salt or complex catalyst is generally required selectively activate couple the carbene, metals employed far are expensive (Rh, Au, Ag, Cu) often unrecoverable. It noteworthy that price ligands can make cheaper (i.e., other ligand-free noble catalysts. In realm modern sustainable chemistry, most these methodologies now unacceptable must adapted, simple strategies for include carbene photoactivation use recoverable solid Unfortunately, despite research field insertion reactions has extended more than 50 years, examples with catalysts still minor, efficient only been reported last two decades.This Account shows journey faced by our group eight years find challenging reactions, employing diazocarbonyl precursors. We will contextualize results those previous The discovery 2017 quasi-linear Pd4 cluster stabilized within metal-organic framework (MOF) was able catalyze Büchner spurred design supported clusters reactions. Pd4-MOF could reused 20 times batch implemented flow process. Following this, catalytic solids, including Au Ag metals, not same MOF but also on oxides zeolites supports, showed good activity were reusable.Our temporarily finishes 2024 when "blank" experiments dealuminated zeolite surprisingly revealed this acid, without any metal, easily activates compound catalyzes thus providing cheap, commercially available, reusable Overall, rapid progress solid-catalyzed activation, formation, achieved during moving from difficult prepare based acid zeolites, pointing confined Brønsted acids study near future.

Язык: Английский

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Catalytic Atroposelective Construction of Diarylethers and Diarylamines

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 7891 - 7911

Опубликована: Апрель 29, 2025

Язык: Английский

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Desymmetric esterification catalysed by bifunctional chiral N-heterocyclic carbenes provides access to inherently chiral calix[4]arenes

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Май 13, 2025

Язык: Английский

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Catalytic Enantioselective Synthesis of Axially Chiral Diaryl Ethers Via Asymmetric Povarov Reaction Enabled Desymmetrization

Advanced Science, Год журнала: 2024, Номер unknown

Опубликована: Июль 16, 2024

Axially chiral diaryl ethers represent a distinct class of atropisomers, characterized by unique dual C─O axes system, which have been found in variety natural products, pharmaceuticals, and ligands. However, the catalytic enantioselective synthesis these atropoisomers poses significant challenges, due to difficulty controlling both axes, their more flexible conformations. Herein, an efficient protocol for axially is presented using organocatalyzed asymmetric Povarov reaction-enabled desymmetrization, followed aromatizations. This method yields wide range novel quinoline-based ether good high enantioselectivities. Notably, various aromatization protocols are developed, resulting diverse set polysubstituted quinoline-containing atropisomers. Thermal racemization studies suggested excellent configurational stabilities atropisomers (with barriers up 38.1 kcal mol

Язык: Английский

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N-Heterocyclic carbene (NHC) organocatalysis: from fundamentals to frontiers

Chemical Society Reviews, Год журнала: 2024, Номер unknown

Опубликована: Дек. 18, 2024

This tutorial review provides an overview of various important structural features and reactivity modes NHCs delves deep into the recent advances in NHC-organocatalysis.

Язык: Английский

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Enabling Construction of Boron-Stereogenic Formyl BODIPYs via N-Heterocyclic Carbene-Catalyzed Enantioselective Esterification

JACS Au, Год журнала: 2025, Номер unknown

Опубликована: Май 16, 2025

Язык: Английский

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