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

Organic Letters, Год журнала: 2024, Номер 26(18), С. 3790 - 3795

Опубликована: Апрель 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.

Язык: Английский

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Synthesis of Highly Functionalized Indolizines via NIS-Promoted Spiroannulation/Ring-Opening Aromatization of Alkylidene Oxindoles with 2-(Pyridin-2-yl)acetate Derivatives

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

Опубликована: Март 10, 2025

A novel NIS-promoted domino reaction of alkylidene oxindoles with 2-(pyridin-2-yl)acetate derivatives has been established, enabling the efficient and straightforward synthesis a vast variety highly functionalized indolizines via sequential spiroannulation ring-opening aromatization processes. The protocol features mild conditions, broad substrate scope, high efficiency, scalability, applicability for preparation CF3-containing indolizines. Furthermore, functional groups in indolizine framework provide feasibility follow-up derivatization. Based on mechanistic studies, plausible radical mechanism is proposed to elucidate formation

Язык: Английский

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NHC-Catalyzed Reaction of Aldehydes for C(sp2)–O Bond Formation

Catalysts, Год журнала: 2024, Номер 14(4), С. 219 - 219

Опубликована: Март 22, 2024

In the past few decades, N-heterocyclic carbenes (NHCs) have opened new field of organocatalysis in synthetic organic chemistry. This review highlights dramatic progress NHC-catalyzed C–O bond formation based on activation aldehyde C(sp2)–H bonds. The oxidative and redox transformations for synthesis various molecules with structural diversity complexity are summarized. Furthermore, methods strategies NHC catalysis emerging continuously; thus, cooperative Brønsted acid, hydrogen-bonding catalyst, transition-metal photocatalyst also described.

Язык: Английский

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COAP‐Pd Catalyzed Asymmetric Formal [3+2] Cycloaddition for Optically Active Multistereogenic Spiro Cyclopentane‐Indandiones Bearing Cyclic N‐Sulfonyl Ketimine Skeletons

Chemistry - An Asian Journal, Год журнала: 2024, Номер 19(12)

Опубликована: Апрель 17, 2024

Abstract We reported a chiral oxamide‐phosphine ligand (COAP−Ph)‐Pd‐catalyzed asymmetric [3+2] cycloaddition reaction between vinyl cyclopropane compounds derived from 1,3‐indanedione and 2‐vinylcyclopropane‐1,1‐dicarboxylates with cyclic sulfonyl 1‐azadienes. The corresponding reactions provided series of enantiomerically active spiro cyclopentane‐indandione cyclopentane structures bearing three consecutive stereogenic centers in good yields diastereo‐ enantioselectivity. COAP−Pd complex serves not only to promote generation π ‐allyl‐palladium intermediates induce the asymmetry reaction, but also depress background reaction.

Язык: Английский

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Regio- and diastereoselective synthesis of thioxothiazolidin-indolin-2-ones, oxoindolin-carbamodithioate hybrids, and their base-catalyzed conversion into dispirocyclopentanebisoxindoles

Scientific Reports, Год журнала: 2024, Номер 14(1)

Опубликована: Июнь 20, 2024

Abstract In this publication, we reported a regio-, diastereoselective, and kinetically controlled reaction for synthesizing thioxothiazolidin-indolin-2-ones, oxoindolin-carbamodithioate hybrids, their base-catalyzed conversion into dispirocyclopentanebisoxindoles. Obtaining only the kinetic thioxothiazolidin-indolin-2-one products together with straightforward to dispirocyclopentanebisoxindoles, excellent regio- diastereoselectivity, easy workup, one-pot synthetic operation are considerable advantages of work.

Язык: Английский

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Catalyst-free rapid crystallization-induced stereoselective three-component [3 + 2] cycloaddition to polycyclic spirooxindoles under microwave irradiation

Research on Chemical Intermediates, Год журнала: 2024, Номер 50(3), С. 1497 - 1509

Опубликована: Янв. 29, 2024

Язык: Английский

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Dearomative (3 + 2) Cycloaddition of Indoles for the Stereoselective Assembly of Fully Functionalized Cyclopentanoids

Organic Letters, Год журнала: 2024, Номер 26(19), С. 4077 - 4081

Опубликована: Май 2, 2024

The gold(I)-catalyzed dearomative cyclopentannulation of various indoles with 2-ethynyl-1,3-dithiolane is reported. method generates three new stereocenters excellent control relative stereochemistry and tolerant diverse functionalization substitution patterns on the indoles. obtained cyclopentane-fused indolines allow for interesting subsequent synthetic manipulations, giving rise to fully substituted cyclopentanes all five stereocenters. reported reaction illustrates elucidates a mechanistic dichotomy underlying reactions 2-ethynyl-1,3-dithiolane.

Язык: Английский

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Regio- and diastereoselective synthesis of thioxothiazolidin- indolin-2-ones, oxoindolin-carbamodithioate hybrids, and their base-catalyzed conversion into dispirocyclopentanebisoxindoles

Research Square (Research Square), Год журнала: 2024, Номер unknown

Опубликована: Май 15, 2024

In this publication, we reported a regio-, diastereoselective, and kinetically controlled reaction for synthesizing thioxothiazolidin-indolin-2-ones, oxoindolin-carbamodithioate hybrids, their base-catalyzed conversion into dispirocyclopentanebisoxindoles. Obtaining only the kinetic thioxothiazolidin-indolin-2-one products together with straightforward to dispirocyclopentanebisoxindoles, excellent regio- diastereoselectivity, easy workup, one-pot synthetic operation are considerable advantages of work.

Язык: Английский

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Five-membered ring systems: Pyrroles and benzo analogs

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 123 - 173

Опубликована: Янв. 1, 2024

Язык: Английский

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Six-membered ring systems: With O and/or S atoms

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 421 - 484

Опубликована: Янв. 1, 2024

Язык: Английский

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