Type of Tetrahydronaphthalene-Fused 1,5-Dipoles and Their Application in Polycyclic Compounds Synthesis DOI
Zhengyu Han,

Xue Yu,

Hongling Xie

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10551 - 10556

Published: July 17, 2024

Palladium-catalyzed dipolar cycloaddition reactions represent an efficient strategy for the construction of cyclic compounds, with development novel precursors being a key focus. In this study, new type precursor was synthesized through assembly vinylethylene carbonate unit and tetrahydronaphthalene skeleton. This can undergo [3 + 2], [5 4], 2] reactions, leading to tetrahydronaphthalene-fused oxazolidin-2-ones, 1,5-oxazonines, tetrahydrooxepines. general, all these exhibited good reaction efficiency functional group tolerance.

Language: Английский

Palladium-catalyzed decarboxylative (4 + 3) cycloadditions of bicyclobutanes with 2-alkylidenetrimethylene carbonates for the synthesis of 2-oxabicyclo[4.1.1]octanes DOI Creative Commons

X. N. Gao,

Lei Tang, Xu Zhang

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(34), P. 13942 - 13948

Published: Jan. 1, 2024

While cycloaddition reactions of bicyclobutanes (BCBs) have emerged as a potent method for synthesizing (hetero-)bicyclo[

Language: Английский

Citations

23
Enantioselective Pd- and Cu-Catalyzed Hydrofunctionalization of Methylenecyclopropanes via a Distal C–C Bond Cleavage DOI
Jie Zhao,

Deyue Ren,

Jintao Xia

et al.

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

Published: Jan. 28, 2025

The enantioselective ring-opening reactions of methylenecyclopropanes (MCPs) involving C–C bond activation via oxidative addition transition metals have been rarely reported. Here, we disclose a Pd/Cu-catalyzed enantio- and regioselective coupling between cyclic imino esters MCPs to produce α-allylated 2H-pyrrole derivatives. In this reaction, azomethine ylide formed by chiral copper catalyst with ketimine ester would serve as nucleophile react activated palladium catalysis. This bimetallic system exhibited broad substrate scope high regio- enantioselectivities.

Language: Английский

Citations

0
Palladium-catalyzed [4+4] cycloaddition of 2-pyrones with 2-alkylidenetrimethylene carbonates: access to bridged eight-membered oxygen heterocycles DOI

Huawei Lin,

Biming Mao, Bing Han

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2864 - 2869

Published: Jan. 1, 2024

A novel palladium-catalyzed [4 + 4] cycloaddition of 2-pyrones with 2-alkylidenetrimethylene carbonates has been developed for the synthesis bridged eight-membered oxygen heterocycles in good yields and excellent stereoselectivities.

Language: Английский

Citations

2
Synthesis of Indole‐Fused Eight‐Membered Oxa‐Rings via Palladium‐Catalyzed Asymmetric [4+4] Cycloaddition of Indole‐2,3‐Quinodimethanes with 2‐Alkylidenetrimethylene Carbonates DOI
Xinhao Lu, Yì Wáng,

Chenghan He

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 16, 2024

Comprehensive Summary We report a palladium‐catalyzed asymmetric [4+4] cycloaddition reaction between 2‐alkylidenetrimethylene carbonate and electron‐deficient indole‐2,3‐quinodimethanes ( IQDMs ). This features exclusive regioselectivity, high yield (up to 98%), excellent enantioselectivity 95% ee), easy scale‐up without any loss of efficiency, making it valuable for the synthesis indole‐fused eight‐membered oxa‐rings.

Language: Английский

Citations

1
Palladium-Catalyzed Cycloaddition Reactions of π–Allylpalladium 1,4-Dipoles with 1,3,5-Triazinanes: Access to Hexahydropyrimidines, 1,3-Oxazinanes, and 1,5-Diazocanes DOI
Xinhua Zhang,

Zhi‐Hui Wang,

Yan Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8363 - 8375

Published: June 7, 2024

Palladium-catalyzed decarboxylation of 5-methylene-1,3-oxazinan-2-ones and 5-methylene-1,3-dioxan-2-ones to generate aza-π-allylpalladium oxa-π-allylpalladium 1,4-dipoles for [4 + 2] cycloaddition reaction with 1,3,5-triazinanes was developed, affording a wide range hexahydropyrimidine 1,3-oxazinane derivatives in good excellent yields (up 99%). The acyclic sulfonamido-substituted allylic carbonates as 1,4-dipole precursors also apply the developed synthesized strategy, achieving synthesis hexahydropyrimidines. Moreover, situ-generated undergoing dimeric 4] were demonstrated by construction 1,5-diazocane derivatives.

Language: Английский

Citations

0
Ytterbium‐Catalyzed Tandem Diels–Alder/Claisen Rearrangement/Decarboxylation of Hetero‐Allenes for the Synthesis of Diarylmethanes DOI
Bin Chen, Shan Zhong,

Huilin Zhan

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 43(2), P. 199 - 204

Published: Oct. 17, 2024

Comprehensive Summary A tandem Diels–Alder reaction/Claisen rearrangement/decarboxylation strategy of N ‐allenamides (or aryloxyallenes) with 3‐alkoxycarbonyl‐2‐pyrones has been developed for the efficient synthesis diarylmethanes moderate to good yields. The reaction exhibits functional group tolerance and can be applied late‐stage modifications known drug molecules. Mechanistic studies indicate that ester at 3‐position 2‐pyrones is essential, initial between proximal C=C bond crucial success reaction.

Language: Английский

Citations

0
Copper‐Catalyzed Formal [4+2] Cycloaddition of Ethynylethylene Carbonates for the Construction of 3,4‐Dihydro‐2H‐benzo[b][1,4]oxazines DOI

Xinzhe Hu,

Haihui Zhu,

Xiang Li

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(25)

Published: April 9, 2024

Abstract A formal [4+2] cycloaddition reaction of ethynylethylene carbonates and 2‐aminophenols has been developed for the synthesis 3,4‐dihydro‐2 H ‐benzo[ b ][1,4]oxazines bearing quaternary carbon atoms. The features mild conditions, good functional group compatibility yields. Furthermore, when using chiral PyBox ligand, this strategy could also achieve asymmetric ][1,4]oxazines. Application studies indicated that hydroxymethyl final products was an excellent can be further modified easily.

Language: Английский

Citations

0
Unraveling the Potential of Cyclic N‐Sulfonyl Ketimines in the MCR Universe DOI Creative Commons

Michael Fragkiadakis,

Eirini Fotopoulou, Konstantinos G. Froudas

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: July 31, 2024

Abstract Cyclic N ‐sulfonyl ketimines constitute an accessible class of lead‐like heterocycles with a vast application in both synthetic organic and medicinal chemistry. In this context, we harness the capabilities these four different isocyanide‐based multicomponent reactions. Our goal was to create libraries compounds functional groups vectors that are compatible for structural elaboration optimization their physical properties. We synthesized 15 unprecedented high diversity complexity, whereas have obtained single crystal structures each scaffold, unraveling geometrical features potential employment drug discovery.

Language: Английский

Citations

0
Type of Tetrahydronaphthalene-Fused 1,5-Dipoles and Their Application in Polycyclic Compounds Synthesis DOI
Zhengyu Han,

Xue Yu,

Hongling Xie

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10551 - 10556

Published: July 17, 2024

Palladium-catalyzed dipolar cycloaddition reactions represent an efficient strategy for the construction of cyclic compounds, with development novel precursors being a key focus. In this study, new type precursor was synthesized through assembly vinylethylene carbonate unit and tetrahydronaphthalene skeleton. This can undergo [3 + 2], [5 4], 2] reactions, leading to tetrahydronaphthalene-fused oxazolidin-2-ones, 1,5-oxazonines, tetrahydrooxepines. general, all these exhibited good reaction efficiency functional group tolerance.

Language: Английский

Citations

0