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

Biao Du,

Qiumi Wang

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(35), P. 15446 - 15451

Published: Jan. 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.

Language: Английский

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

Yi Li,

Xianfei Hu,

Boning Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 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.

Language: Английский

Citations

4
Pyridine-Catalyzed Chemoselective Four-Component Cascade Reaction of Aromatic Aldehydes, Malononitrile/Cyanoacetates, MBH Carbonates, and Alcohols DOI
Boning Li,

Xianfei Hu,

Hui Yao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7576 - 7583

Published: Sept. 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

Language: Английский

Citations

3
Visible-Light-Promoted Iron(II)/Lewis Base Catalysis for the Alkylation of Morita–Baylis–Hillman Acetates Using Carboxylic Acids DOI

Durga Golagani,

Kota Krishna Prakash,

Satyam Thapa

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 1, 2024

A novel photoinduced Fe(OTf)

Language: Английский

Citations

3
Merging Enantioselective Lewis Base Organocatalysis and Gold(I) Catalysis: A One-Pot Access to Chiral-Fused Polycyclic Compounds DOI

Rémi Pereira,

Pierre Locquet,

Aurélien Blanc

et al.

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

Citations

0
Directing Group-Controlled Regioselective [4 + 3] Annulation of Indole-2-Carboxamides with MBH Carbonates toward Highly Substituted Indole-1,2-Fused Diazepanones DOI
Shutao Wang, W. Y. Zhang,

Zhuoqi Zhang

et al.

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

Published: April 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.

Language: Английский

Citations

0
NHC/Pd Synergistically Catalyzed Direct Aerobic Oxidative Allylic Esterification of Aldehydes DOI
Chhanda Debnath, Shikha Gandhi

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 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.

Language: Английский

Citations

0
DABCO-catalyzed mono- and bisallylation of β,γ-unsaturated ketones with Morita-Baylis-Hillman carbonates DOI
Guizhou Yue,

Biao Du,

Qiumi Wang

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(35), P. 15446 - 15451

Published: Jan. 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.

Language: Английский

Citations

0