Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown
Опубликована: Дек. 17, 2024
Abstract A variety of structurally diverse spirocyclohexane oxindoles featuring a quaternary carbon centre have been successfully constructed through an N‐heterocyclic carbene‐catalyzed [4+2] annulation isatin‐derived enals with α ‐cyano‐ β ‐methylenones. This domino process exhibits wide substrate tolerance, operates under mild conditions, and yields products high enantioselectivities.
Язык: Английский
Chemistry - An Asian Journal, Год журнала: 2024, Номер 19(9)
Опубликована: Март 7, 2024
N-Heterocyclic carbenes (NHCs) catalysts have been employed as effective tools in the development of various reactions, which made notable contributions developing diverse reaction modes and generating significant functionalized molecules. This review provides an overview recent advancements chemo- regioselective activation different aldehydes using NHCs, categorized into five parts based on modes. A brief conclusion outlook is provided to stimulate novel for accessing functional
Язык: Английский
Процитировано
5
Arabian Journal of Chemistry, Год журнала: 2024, Номер 17(8), С. 105845 - 105845
Опубликована: Май 23, 2024
Cyclopropenone has emerged as a highly versatile precursor in organic synthesis due to its diverse reactivity. The cyclopropenone derivatives could undergo various transformations such cycloaddition reactions, ring-opening and isomerization reactions the presence of different chemical reagents. Over years, significant progress been made manipulation cyclopropenones for construction carbocycles, heterocycles, other useful compounds. Despite several reviews that have concerned chemistry cyclopropenones, utility motifs carbocycles heterocycles rarely reported. Herein, we report recent advancements synthetic precursors towards compounds with biological significance.
Язык: Английский
Процитировано
4
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
Процитировано
4
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
Процитировано
3
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Янв. 9, 2025
In this work, we developed a phosphine-catalyzed cascade lactonization/[2 + 1] annulation reaction between vinyl oxiranes and sulfonium compounds for the highly diastereoselective construction of spiro-2(3H)-furanone skeletons. The cycloaddition proceeds via 2(5H)-furanone phosphonium intermediate, introducing an oxygen-containing active intermediate phosphine catalysis. These findings highlight significant potential harnessing as versatile synthons constructing spirocyclic through simultaneous multicyclic skeleton formation.
Язык: Английский
Процитировано
0
European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(28)
Опубликована: Май 27, 2024
Abstract A straightforward [3+2] annulation method for synthesizing bisspiro(oxindole) derivatives has been developed by using isatin‐derived Morita‐Baylis‐Hillman carbonates and p ‐quinone methides ( ‐QMs) with 4‐dimethylaminopyridine (DMAP) as the catalyst. The optimized protocol in dichloromethane (DCM) solvent achieves good yields (up to 87 %) diastereoselectivity (>20 : 1). versatility of is shown through synthesis various derivatives, including chiral variants up 82 % ee. intermediates were captured HRMS, a plausible reaction pathway was proposed.
Язык: Английский
Процитировано
2
Organic Letters, Год журнала: 2024, Номер 26(43), С. 9322 - 9327
Опубликована: Окт. 24, 2024
The present work develops a DMAP-catalyzed [3 + 2] cycloaddition of vinyl oxiranes with activated ketone compounds, affording dioxolane derivatives moderate to excellent yields. This approach represents the first Lewis base (LB)-catalyzed ring-opening reaction epoxides, simultaneously providing rare oxygen-containing active intermediate in this field. gram-scale preparation and facile derivatization cycloadduct highlight significant synthetic potential strategy.
Язык: Английский
Процитировано
2
Molecules, Год журнала: 2024, Номер 29(8), С. 1790 - 1790
Опубликована: Апрель 15, 2024
A chemselective catalyst-free three-component 1,3-dipolar cycloaddition has been described. The unique polycyclic THPI and THIQs were creatively employed as dipolarophiles, which led to the formation of functionalized β-tetrahydrocarboline- tetrahydroisoquinoline-fused spirooxindoles in 60–94% yields with excellent diastereoselectivities (10: 1−>99: 1 dr). This reaction not only realizes a concise THPI- or THIQs-based cycloaddition, but also provides practical strategy for construction two distinctive spirooxindole skeletons.
Язык: Английский
Процитировано
1
Chemical Science, Год журнала: 2024, Номер unknown
Опубликована: Янв. 1, 2024
Combined experimental and quantum-chemical studies were used to characterise the philicity/fugality features of tertiary phosphines Michael acceptors in phospha-Michael reactions, which are key steps phosphine-catalysed organic reactions.
Язык: Английский
Процитировано
1
Journal of Molecular Structure, Год журнала: 2024, Номер unknown, С. 140434 - 140434
Опубликована: Окт. 1, 2024
Язык: Английский
Процитировано
1