Cooperative Gold(I)/DMAP Catalysis Enabled (2 + 3) Cycloadditions of Yne–Enones with Oxindole-Derived MBH Carbonates

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3790 - 3795

Published: April 26, 2024

A cooperative gold(I)/DMAP system catalyzes the (2 + 3) cycloadditions of yne-enones with oxindole-derived Morita-Baylis-Hillman (MBH) carbonates, yielding diverse bispiro-cyclopentene oxindole products. The mild, scalable protocol demonstrates broad substrate scope and excellent chemo- diastereoselectivity. Mechanistic study reveals pivotal roles both catalysts in unique cycloaddition. This strategy showcases superiority achieving transformation chemoselectivity diastereoselectivity, unattainable through traditional monocatalytic methodologies.

Language: Английский

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Merging Enantioselective Lewis Base Organocatalysis and Gold(I) Catalysis: A One-Pot Access to Chiral-Fused Polycyclic Compounds

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 21, 2025

Reported herein is a route to functionalized chiral heteroaromatic polycyclic compounds leveraging two unfriendly catalytic cycles in one-pot sequential process. α-Heteroaromatic-γ-butyrolactones were engaged highly regio-, diastereo-, and enantio-selective Lewis base asymmetric allylic alkylation (AAA) with alkyne-functionalized Morita–Baylis–Hillman (MBH) carbonates. Gratefully, due the low catalyst loading, subsequent gold-catalyzed Friedel–Crafts type cyclization, entailing formation of fused compounds, proceeded efficiently, affording structurally complex, enantioenriched products.

Language: Английский

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

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: April 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.

Language: Английский

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Enantioselective gold/enzyme dual catalysis

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: unknown, P. 155382 - 155382

Published: Nov. 1, 2024

Language: Английский

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Enantioselective and Regiodivergent Gold and Chiral Brønsted Acid Catalyzed Cycloisomerization/Diels–Alder Reaction of 1,10-Dien-4-yn-3-yl Acetates: Synthesis of Norbornene-Embedded Tricarbocycles

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3037 - 3042

Published: April 1, 2024

A synthetic method for the enantioselective and regiodivergent synthesis of hexahydro-2H-2,4a-methanonaphthalen-4-yl octahydro-2,4-methanoazulen-1-yl esters that relies on gold(I)- chiral Brønsted acid-catalyzed cycloisomerization/Diels–Alder (CDA) reaction (E)-1,10-dien-4-yn-3-yl acetates is described.

Language: Английский

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Enantioselective Synthesis of α‐Quaternary Isochromanes by Oxidative Aminocatalysis and Gold Catalysis

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(38)

Published: April 17, 2024

Abstract A novel strategy that combines oxidative aminocatalysis and gold catalysis allows the preparation of chiral α‐quaternary isochromanes, a motif is prevalent in natural products synthetic bioactive compounds. In first step, α‐branched aldehydes propargylic alcohols are transformed into ethers with excellent optical purities (>90 % ee ) via umpolung DDQ an amino acid‐derived primary amine catalyst. Subsequent gold(I)‐catalyzed intramolecular hydroarylation affords isochromane retention quaternary stereocenter. second approach explores use allylic as reaction partners for coupling to furnish generally lower enantiopurities. Stereoretentive cyclization achieved Friedel‐Crafts type alkylation acetates reactive handle. number elaborations biological study on these isochromanes highlight potential applicability presented method.

Language: Английский

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Consecutive Chirality Transfer: Efficient Synthesis of Chiral C,O-Chelated BINOL/Gold(III) Complexes for Asymmetric Catalysis and Chiral Resolution of Disubstituted BINOLs

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Diastereomeric resolution of C,O-chelated BINOL/gold( iii ) complexes was demonstrated, in which the recovered gold( dichloride could resolve BINOL derivatives. This new class achieved asymmetric catalysis with up to 99% ee.

Language: Английский

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Enantioselective Au(I)-Catalyzed Cycloisomerization/Addition of Oxygen Nucleophiles to 2-Alkynylenones by the Tethered Counterion-Directed Catalysis Strategy

Organic Letters, Journal Year: 2024, Volume and Issue: 26(44), P. 9525 - 9530

Published: Oct. 29, 2024

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