Construction of α-Acyloxy Ketones via Photoredox-Catalyzed O–H Insertion of Sulfoxonium Ylides with Carboxylic Acids

Organic Letters, Год журнала: 2023, Номер 25(36), С. 6613 - 6617

Опубликована: Сен. 6, 2023

Herein, a photoredox-catalyzed insertion of sulfoxonium ylides with carboxylic acids was advanced under mild and simple conditions, offering practical approach for preparing α-acyloxy ketones broad scope acids. A combined experimental computational study suggests that this reaction proceeds via stepwise proton-assisted electron transfer mechanism.

Язык: Английский

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Photochemical Functionalization of 4-Diazoisoquinoline-1,3(2H,4H)-diones and Their 1-Sulfoxide Analogues

ACS Organic & Inorganic Au, Год журнала: 2025, Номер unknown

Опубликована: Март 24, 2025

Язык: Английский

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Theoretical Analysis of a Three-Component Reaction between Two Diazo Compounds and a Hydroxylamine Derivative: Mechanism, Enantioselectivity, and Effect of Cooperative Catalysis

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(24), С. 17215 - 17226

Опубликована: Ноя. 30, 2023

The mechanism, enantioselectivity, and effect of chiral phosphoric acid (CPA) cocatalyst were investigated by the density functional theory (DFT) for three-component asymmetric aminohydroxylation between two diazo compounds a hydroxylamine derivative. This type cascade process is cooperatively catalyzed Rh2(OAc)4 CPA. obtained results clearly indicate that first step global reaction involves nucleophilic attack at nitrogen center N-hydroxyaniline rhodium-carbene intermediates producing imines. Subsequently, an enolate intermediate was recognized as key species generated from second compound leaving benzyl alcohol (BnOH) fragment in presence same dirhodium catalyst. Then, terminated Mannich-type addition, delivering products S-R conformation with assistance acid. distortion/interaction analysis shows relative distortions CPA enol play vital role energy ordering stereocontrolling transition states (TSs). Furthermore, influence different substituents fully rationalized analysis. study opens up novel synthetic possibilities improves predictability when exploring related types organic transformations.

Язык: Английский

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Modular synthesis of conjugated enamidines and cascade annulation toward benzofuran-3-oxoacetate

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(7), С. 2047 - 2053

Опубликована: Янв. 1, 2024

A three-component reaction of aryne, DMF and isonitrile for the synthesis otherwise inaccessible chemotype, conjugated enamidines, is developed. Incubation with a Brønsted acid causes cascade skeleton rearrangement enamidines to benzofuran-3-oxoacetates.

Язык: Английский

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