Gold-catalyzed cyclization and cycloaddition in natural product synthesis

Natural Product Reports, Год журнала: 2024, Номер 41(7), С. 1091 - 1112

Опубликована: Янв. 1, 2024

This review highlights a curated selection of publications utilizing homogeneous gold-catalyzed cycloaddition and cyclization reactions for the total synthesis natural products reported from 2016 to mid-2023.

Язык: Английский

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Gold-based enantioselective bimetallic catalysis

Chemical Communications, Год журнала: 2023, Номер 59(52), С. 8007 - 8016

Опубликована: Янв. 1, 2023

Multimetallic catalysis is a powerful strategy to access complex molecular scaffolds efficiently from easily available starting materials.

Язык: Английский

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Enantioselective and Diastereodivergent Allylation of Propargylic C–H Bonds

Journal of the American Chemical Society, Год журнала: 2022, Номер 144(34), С. 15480 - 15487

Опубликована: Авг. 17, 2022

An iridium-catalyzed stereoselective coupling of allylic ethers and alkynes to generate 3,4-substituted 1,5-enynes is reported. Under optimized conditions, the products are formed with excellent regio-, diastereo-, enantioselectivities, protocol functional group tolerant. Moreover, we report conditions that allow reaction proceed complete reversal diastereoselectivity. Mechanistic studies consistent an unprecedented dual role for iridium catalyst, enabling propargylic deprotonation alkyne through π-coordination, as well generation a π-allyl species from ether starting material.

Язык: Английский

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Chiral Ligands for Au(I), Au(III), and Au(I)/Au(III) Redox Catalysis

Israel Journal of Chemistry, Год журнала: 2022, Номер 63(9)

Опубликована: Авг. 29, 2022

Abstract Gold catalysis has emerged as an efficient tool for the selective functionalisation of C−C multiple bonds. Despite significant progress in this field, potential asymmetric gold not been fully explored to date. A historical retrospect on area reveals that enantioselective is based three pillars: Au(I) catalysis, Au(III) and Au(I)/Au(III) redox catalysis. Irrespective mode being operative, design new ligands crucial development gold‐catalysed organic transformations. This minireview summarizes made ligand focusing which were specially designed

Язык: Английский

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Chiral Auxiliary Approach for Gold(I)‐Catalyzed Cyclizations

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(49)

Опубликована: Окт. 24, 2023

Two different classes of stereoselective cyclizations have been developed using a chiral auxiliary approach with commercially available [JohnPhosAu(MeCN)SbF6 ] as catalyst. First, cascade cyclization 1,5-enynes was achieved the Oppolzer camphorsultam auxiliary. In this case, one-pot cyclization-hydrolysis sequence to directly afford enantioenriched spirocyclic ketones. Then, alkoxycyclization 1,6-enynes mediated by an Evans-type oxazolidinone. A reduction-hydrolysis selected remove give β-tetralones. DFT studies confirmed that steric clash between and alkene accounts for experimentally observed diastereoselective through Si face.

Язык: Английский

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Desymmetrization and Parallel Kinetic Resolution of 1-Ethynylcyclobutanols via Asymmetric Cooperative Gold Catalysis

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(50), С. 27205 - 27210

Опубликована: Дек. 8, 2023

Enantioselective gold catalysis remains a challenging area of research. By harnessing gold-ligand cooperation in the presence chiral bifunctional phosphine ligand featuring novel 3'-phosphine oxide moiety, highly enantioselective desymmetrization 1-ethynylcyclobutanols is achieved, permitting access to α-methylenecyclopentanones diverse array quaternary and tertiary centers. This cooperative also enables parallel kinetic resolution catalysis, delivering cyclopentanone regioisomers with excellent enantiomeric excesses. DFT calculations transition states support distinct mechanism asymmetric induction via controlling conformation bound substrate hence dictating ring bond undergoing migration.

Язык: Английский

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Supramolecular networks featuring diverse array of noncovalent interactions in crystals of hydrazinylidene-benzothiazinediones: X-ray crystallographic, DFT and biochemical analysis

Journal of Molecular Structure, Год журнала: 2024, Номер 1306, С. 137840 - 137840

Опубликована: Фев. 21, 2024

Язык: Английский

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Gold(I)-Catalyzed Cycloisomerization–Indole Addition Cascade: Synthesis of 3(2H)-Furanone-Incorporated Unsymmetrical 3,3′- Bis(indolyl)methanes

Organic Letters, Год журнала: 2022, Номер 24(27), С. 4930 - 4934

Опубликована: Июль 1, 2022

An unprecedented Au(I)-catalyzed domino intramolecular carbonyl-alkyne cyclization/indole addition strategy has been disclosed here. This generalized enables the synthesis of 3(2H)-furanone-incorporated unsymmetrical bis(indolyl)methanes with generation a stereocenter at furanone junction from easily accessible indole-tethered ynediones. In addition, this present protocol could also be extended for number indolyl-(hetero)arylmethanes by employing variety (hetero)arenes as nucleophile coupling partner.

Язык: Английский

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Gold‐Catalyzed Alkyne‐Amine Cascade Annulations: A Modern Strategy for Azaheterocycle Construction

The Chemical Record, Год журнала: 2025, Номер unknown

Опубликована: Апрель 7, 2025

Abstract Gold catalysis has experienced remarkable progress over the past two decades, particularly in transformations involving alkynes. While numerous aspects of gold‐catalyzed reactions have been extensively reviewed, specific area cascade annulations between functionalized amines and alkynes represents a distinct rapidly developing direction that warrants focused attention. This survey collects systematically analyzes these transformations, which emerged as convenient synthetic strategies to diverse nitrogen heterocycles. The relevant are classified firstly by chemical nature amine functional substituent, secondly size formed ring. field under consideration bridges several fundamental practical branches chemistry, including catalysis, organic synthesis, medicinal materials science.

Язык: Английский

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Organic Peroxides in Transition-Metal-Free Cyclization and Coupling Reactions (C–C) via Oxidative Transformation

ACS Omega, Год журнала: 2025, Номер unknown

Опубликована: Апрель 14, 2025

Transition-metal-free transformations are recognized as green and sustainable methods for constructing carbon-carbon bonds in organic synthesis. This review describes the application of six peroxides, including tert-butyl hydroperoxide (TBHP), di-tert-butyl peroxide (DTBP), peroxybenzoate (TBPB), benzoyl (BPO), dialauroyl (DLP), diguyl (DCP), C-C bond construction, highlighting selected examples mechanisms challenging transformations. Each section concludes with a detailed overview suitable reagents various coupling reactions strengths weaknesses reported works. work aims to inspire further innovations transition-metal-free oxidative transformations, promoting eco-friendly chemical processes paving way new peroxide-based synthesis methods.

Язык: Английский

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