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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Sc-Catalyzed Asymmetric [2 + 2] Annulation of 2-Alkynylnaphthols with Dienes to Access Cyclobutene Frameworks

Organic Letters, Год журнала: 2025, Номер 27(4), С. 1006 - 1011

Опубликована: Янв. 16, 2025

Herein, we introduce a scandium-catalyzed synthetic strategy that provides access to diverse and functionalized array of cyclobutene frameworks adorned with quaternary carbon center. This approach broadens the repertoire 2-alkynylnaphthols alkenes, offering versatile platform for construction complex molecular architectures. The asymmetric catalytic [2 + 2] cycloaddition reaction demonstrates wide substrate scope an impressive functional group tolerance, yielding products high efficiency, up 97% yield, excellent enantiomeric excess 97%. simplicity scaling this process, coupled ease converting these into variety substituted products, significantly enhances utility method.

Язык: Английский

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Organocatalytic Atroposelective Construction of Pentatomic Heterobiaryl Diamines through Arylation of 5-Aminoisoxazoles with Azonaphthalenes

Organic Letters, Год журнала: 2024, Номер 26(13), С. 2564 - 2568

Опубликована: Март 21, 2024

An efficient catalytic asymmetric Michael-type reaction of azonaphthalenes with 5-aminoisoxazoles has been developed. The was based on the utilization a chiral phosphoric acid as catalyst, delivering large panel axially heterobiaryl diamines in generally good yields excellent enantioselectivities. gram-scale and postmodification product demonstrated their potentials synthesis catalysts ligands. This approach not only provides useful method for construction pentatomic scaffolds but also offers new members to diamine family promising applications synthetic medicinal chemistry.

Язык: Английский

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Sc(OTf)3-catalyzed alkyne-carbonyl metathesis-initiated cyclization for accessing naphtho[2,1-b]furan-1-ones under microwave heating

Tetrahedron Letters, Год журнала: 2024, Номер 138, С. 154962 - 154962

Опубликована: Фев. 16, 2024

Язык: Английский

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Synthesis of 1,5-Diamino-Substituted 1,3-Dienes via Rhodium(II)-Catalyzed Tandem Reactions of 1-Cyclopropylethylarenes

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 18, 2025

Herein, (E,E)-1,5-diamino-1,3-dienes are stereoselectively synthesized from substituted aryl derivatives via a rhodium(II)-catalyzed C(sp3)-H functionalization involving cascade of cyclopropane ring expansion, cyclobutene formation, to 1,3-diene conversion, and regioselective diamination. Mechanistic studies show this one-pot process proceeds through hydrogen atom transfer (HAT), radical-polar crossover (RPC), elimination, electrocyclic ring-opening, radical addition, underscoring rhodium(II)'s role in radical-mediated catalysis beyond traditional rhodium(II) nitrenoid chemistry.

Язык: Английский

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Recent Advances in Catalytic Transformations of ortho-Alkynylnaphthols

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134726 - 134726

Опубликована: Май 1, 2025

Язык: Английский

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Acid-Regulated Selective Synthesis of Benzofuran Derivatives via Single-Component BDA Retro-Aldol/Michael Addition Cascade and [4 + 2] Cycloaddition Reactions

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 20, 2025

The acid-controlled single-component retro-aldol/Michael addition cascade reaction and [4 + 2] cycloaddition of benzofuran-derived azadienes (BDAs) are reported for the first time. Under conditions trifluoromethanesulfonic acid as catalyst with water, BDAs initiate retro-aldol reaction, followed by a 1,4-Michael addition, yielding (arylmethylene)bis(dibenzofuran) products excellent yields broad substrate applicability. This represents application in reaction. In contrast, absence water boron trifluoride etherate catalyst, undergo constructing spiro[benzofuran-2,3'-benzofuro[3,2-b]pyridine] framework high diastereoselectivity. method features mild atom economy, provides new approach benzofuran scaffold derivatives.

Язык: Английский

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Enantioselective Friedel‐Crafts Reaction of ortho‐Alkynylnaphthols with Naphthofurans: Synthesis of Polysubstituted Axially Chiral Styrenes

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(12), С. 2710 - 2714

Опубликована: Май 7, 2024

Abstract Herein, we report a chiral Brønsted acid‐catalyzed enantioselective Friedel‐Crafts reaction of ortho ‐alkynylnaphthols with various naphthofurans, realizing the asymmetric synthesis axially styrenes naphthofurans in 67 to 93% yield and 34 96% ee.

Язык: Английский

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Chiral Brønsted Acid‐Catalyzed Asymmetric Reaction via Vinylidene Ortho‐Quinone Methides

Chemistry - A European Journal, Год журнала: 2024, Номер 30(49)

Опубликована: Июнь 26, 2024

Vinylidene ortho-quinone methides (VQMs) have been proven to be versatile and crucial intermediates in the catalytic asymmetric reaction last decade, thus drawn considerable concentrations on account of practical application construction enantiomerically pure functional organic molecules. However, comparison well established chiral Brønsted base-catalyzed via VQMs, acid-catalyzed is rarely studied there no systematic summary date. In this review, we summarize recent advances VQMs according three types reactions: a) intermolecular nucleophilic addition VQMs; b) cycloaddition c) intramolecular cyclization VQMs. Finally, put forward remained challenges opportunities for potential breakthroughs area.

Язык: Английский

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Proline-based Organocatalyst for the Synthesis of Arylidene Benzofuranone Intermediates Enabling the Construction of Aurone-derived Azadienes

Current Organic Chemistry, Год журнала: 2024, Номер 29(2), С. 127 - 134

Опубликована: Авг. 26, 2024

: Organocatalysis has been recognized as a part of chemical research for long time, and it gained significant attention in catalysis recent decades. Amine catalyst is substantial type organocatalysis, successively employed the activation carbonyl compounds. This manuscript delves into exploration proline-based organocatalyst synthesis arylidene benzofuranone intermediates, critical step that facilitates subsequent construction aurone-derived azadienes. In this work, we successfully reported intermediates through Aldol condensation with different aldehydes enabled by proline-derived organic catalysts. To achieve strategy, six examples amine organocatalysts (A1-A6) were evaluated to showcase optimal transformation. Moreover, further interesting azadiene substrates its reaction TsNH2. Notably, using A6 resulted delivery product best yield (94% isolated yield). Under optimized conditions, aromatic heterocyclic containing effectively tolerated generate corresponding which converted products high excellent yield. The claimed structures confirmed spectral analysis.

Язык: Английский

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