DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes DOI

Dongqiu Li,

Jiale Wu, Lulu Yang

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 20, 2024

Herein, we report a DMAP-catalyzed [4 + 2] annulation reaction of hex-5-en-2-ynoates 1 with electron-poor alkenes 2, which affords exocyclic olefinic cyclohexenes 3 in good yields and excellent regio-, diastereo-, E/Z selectivities. Distinguished from previous allenoate- or alkynoate-based substrates, use the β- ε-carbons for bond formation, presenting new regiodivergent C4 synthons Lewis base-catalyzed annulations.

Язык: Английский

Electrophilic hexa(methoxycarbonyl)cycloheptatrienyl anion in the synthesis of electron-deficient 5-hydroxyisoquinolones DOI

Alexander Yu. Belyy,

Alena D. Sokolova,

Rinat F. Salikov

и другие.

Mendeleev Communications, Год журнала: 2025, Номер 35(2), С. 162 - 164

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

1

Enantioselective phosphine-catalyzed [6 + 1] annulations of α-allyl allenoates with 1,1-bisnucleophiles DOI Creative Commons

Jingxiong Lai,

Wei Cai, You Huang

и другие.

Chemical Science, Год журнала: 2024, Номер 15(29), С. 11515 - 11520

Опубликована: Янв. 1, 2024

Organocatalytic annulations between allenes and bisnucleophiles represent one of the most convenient routes to various carbocycles heterocycles. However, examples are limited formation five- six-membered rings, probably owing relatively easy handling short-chained biselectrophiles. Here we report long-chained α-allyl allenoate-derived 1,6-biselectrophiles for first time, enabling a phosphine catalyzed [6 + 1] annulation with readily available 1,1-bisnucleophilic reagents. The reaction proceeds

Язык: Английский

Процитировано

6

Phosphine-Catalyzed Cascade Cycloaddition of Vinyl Oxiranes with Sulfonium Compounds to Step-Economically Construct Spiro-2(3H)-furanone Scaffolds DOI
Thomas P. Yang, Wei Du,

Chia‐Yu Wu

и другие.

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

Cyсlopentadienone and Pyrone Derivatives as Precursors of Electron-Deficient Cycloheptatrienes: Quantum Chemical Investigation and Synthesis DOI
Rinat F. Salikov, Yury V. Tomilov,

Alena D. Sokolova

и другие.

Synthesis, Год журнала: 2024, Номер 56(16), С. 2581 - 2587

Опубликована: Апрель 30, 2024

Abstract Unstable tetra(methoxycarbonyl)cyclopentadienone was investigated in the synthesis of electron-deficient cycloheptatrienes via [4+2]-cycloaddition/cycloelimination reaction with cyclopropenes. The use its stable dimer did not afford product although similar reactions alkynes have been reported. Quantum chemical calculation revealed that cyclopentadienone is generated from and proceeds a more complicated cycloelimination/cycloaddition/cycloelimination cascade. However, formation found favorable over dimer. Therefore, trapping upon successful to give five ester groups. methyl coumalate as four-electron component cyclopropenes containing only one group two groups product.

Язык: Английский

Процитировано

2

Phosphine-Catalyzed [4 + 1] Annulation of β’-Acetoxy Allenoate with α-Alkylidene Succinimides: Access to Functionalized Spirosuccinimide Derivatives DOI
Chunjie Ni,

Zhanhang Liang,

Xiaojuan Xu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(22), С. 16711 - 16720

Опубликована: Окт. 31, 2024

A phosphine-catalyzed [4 + 1] annulation of β'-acetoxy allenoate with α-alkylidene succinimides is described. This method demonstrates the nucleophilic dialkylation and cyclization succinimides, resulting in formation functionalized spirosuccinimide derivatives. The reaction exhibits a wide substrate scope yields ranging from moderate to excellent under optimized conditions. In addition, biological evaluation indicates that cycloadduct 3u presents satisfied inhibitory activities for three human cancer cell lines (HCT116, A549, HepG2).

Язык: Английский

Процитировано

2

Progress in Synthesis of Medium-Sized Ring Compounds Catalyzed by Organophosphine DOI

Xuling Pan,

You Huang

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(12), С. 3609 - 3609

Опубликована: Янв. 1, 2024

Язык: Английский

Процитировано

2

A highly diastereoselective (5+1) annulation of allenoates and pyrazolones catalyzed by CH3OK DOI

Jingxiong Lai,

You Huang

Chemical Communications, Год журнала: 2024, Номер 60(15), С. 2066 - 2069

Опубликована: Янв. 1, 2024

A CH 3 OK catalyzed [5+1] annulation was developed using a newly designed allene with 1,5-biselectroephilic properties.

Язык: Английский

Процитировано

1

Strategic 1,9-Proton-Transfer-Driven Cycloaddition: Synthesis and Stereoselective Contraction of Nine-Membered Heterocycles DOI

Sekwang Baek,

Ju Young Lee,

Min Jae Kang

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(21), С. 16105 - 16114

Опубликована: Окт. 17, 2024

We introduce a phosphine-catalyzed cycloaddition involving unprecedented long-range intramolecular proton transfer, facilitating the synthesis of nine-membered heterocycles, which are privileged structures in natural products, as well potent pharmacophores. Experimental and computational studies revealed that enamide tether N-aromatic zwitterion directly enables regioselective transfer to proceed independently outer-sphere shuttling. This understanding selective has led improved efficiency regioselectivity desired 1,9-proton reaction under anhydrous conditions, thereby advancing development higher-order reactions. Further stereoselective contraction synthesized cyclic compounds using 3-aza-Cope rearrangement demonstrates synthetic versatility our approach. The findings this study not only advance general mechanism but also broaden its practical utility various chemical fields.

Язык: Английский

Процитировано

1

Synthesis of Benzopyrone-Fused Hydrobenzo[c,d]indoles via Cascade Annulation of p-Quinamines and 3-Formylchromones DOI

Cheng Zhao,

Aiqing Zhong,

Dingxiong Xie

и другие.

Organic Letters, Год журнала: 2024, Номер 26(33), С. 7031 - 7036

Опубликована: Авг. 12, 2024

A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed cascade annulation reaction between

Язык: Английский

Процитировано

0

Rapid Construction of Cycloheptatriene through Organocatalyzed [4 + 3] Annulation of Coumalates DOI

Haiyan Zhang,

Han Xiao, Tong Chen

и другие.

Organic Letters, Год журнала: 2024, Номер 26(36), С. 7495 - 7500

Опубликована: Сен. 5, 2024

A protocol for the construction of cycloheptatrienes has been developed. 4-(Dimethylamino)pyridine (DMAP) was found to be an efficient catalyst promote [4 + 3] annulation between coumalates and γ-alkyl-substituted allenoate or γ-aryl-3-butynoates deliver a variety in moderate good yield with excellent chemoselectivity. The asymmetric version this also realized by using bifunctional phosphine provide chiral products 32-97% ee 29-64% yield.

Язык: Английский

Процитировано

0