Controllable Phosphine-Catalyzed Three-Component Domino Reaction of Activated Alkenes with Morita–Baylis–Hillman (MBH) Carbonates: Divergent Synthesis of Densely Functionalized Cyclopentanes and Diquinanes

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 7, 2024

An unexpected phosphine-catalyzed controllable three-component domino reaction involving [1 + 2 2] annulation and 2]/[3 sequential of 2-arylmethylidene cyanoacetates/malononitriles with Morita-Baylis-Hillman (MBH) carbonates has been developed. A broad range densely functionalized cyclopentanes diquinanes bearing five or four consecutive stereogenic centers, including two all-carbon quaternary stereocenters, were smoothly acquired in moderate to excellent yields under mild conditions from readily available materials. Moreover, this divergent transformation enables the simultaneous generation three new C-C bonds one carbocyclic rings only step.

Язык: 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, Год журнала: 2025, Номер unknown

Опубликована: Фев. 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.

Язык: Английский

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Pyridine-Catalyzed Chemoselective Four-Component Cascade Reaction of Aromatic Aldehydes, Malononitrile/Cyanoacetates, MBH Carbonates, and Alcohols

Organic Letters, Год журнала: 2024, Номер 26(36), С. 7576 - 7583

Опубликована: Сен. 3, 2024

An efficient pyridine-catalyzed chemoselective four-component cascade reaction of aromatic aldehydes, malononitrile/cyanoacetates, Morita-Baylis-Hillman (MBH) carbonates, and alcohols has been established. This one-pot progressed in an unusual with solvent participation via a Knoevenagel condensation/oxa-Michael addition/S

Язык: Английский

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Visible-Light-Promoted Iron(II)/Lewis Base Catalysis for the Alkylation of Morita–Baylis–Hillman Acetates Using Carboxylic Acids

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Окт. 1, 2024

A novel photoinduced Fe(OTf)

Язык: Английский

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Directing Group-Controlled Regioselective [4 + 3] Annulation of Indole-2-Carboxamides with MBH Carbonates toward Highly Substituted Indole-1,2-Fused Diazepanones

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

Опубликована: Апрель 11, 2025

A Lewis base-catalyzed [4 + 3] annulation between dinucleophilic indole-2-carboxamides and Morita-Baylis-Hillmann (MBH) carbonates was developed to access densely substituted indole-1,2-fused diazepanones. This reaction is initiated by a N-allylic alkylation of the indole scaffold with MBH carbonates, followed intramolecular Michael cyclization. Notably, selectivity this process controlled removable o-methoxyphenyl (OMP) directing group attached indole-2-carboxamides. The wide scope substrates, high regio- stereoselectivity, diverse transformations highlight potential synthetic utility method in drug discovery.

Язык: Английский

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NHC/Pd Synergistically Catalyzed Direct Aerobic Oxidative Allylic Esterification of Aldehydes

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 21, 2025

N-Heterocyclic carbene (NHC)-mediated aerobic oxidation of aldehydes has gained interest in recent years. However, its application NHC/Pd synergistic catalysis been unexplored. We have developed a strategy to synthesize allylic esters directly from and Morita-Baylis-Hillman (MBH) carbonates using (cooperative) under conditions. This transformation gives access the selective formation multifunctionalized E-alkenes by β-attack on MBH carbonates. catalytic system also allows use water as cosolvent air sole green oxidant.

Язык: Английский

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DABCO-catalyzed mono- and bisallylation of β,γ-unsaturated ketones with Morita-Baylis-Hillman carbonates

New Journal of Chemistry, Год журнала: 2024, Номер 48(35), С. 15446 - 15451

Опубликована: Янв. 1, 2024

Mono- and bisallylation of β,γ-unsaturated ketones with MBH carbonates in the presence DABCO at rt, offered α-2-alkoxycarbonyl, α,α-di(2-alkoxycarbonyl) α,γ-di(2-alkoxycarbonyl) α,β-unsaturated moderate to excellent yields.

Язык: Английский

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