Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(5), С. 1314 - 1321

Опубликована: Янв. 1, 2024

A new class of chiral bipyridine-2NO ligands, which incorporate the advantages both bipyridine skeleton and pyrroloimidazolone-based N -oxide moiety, was developed.

Язык: Английский

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Py-2NO ligand enabled Ni(ii)-catalyzed asymmetric Michael addition reaction of indoles with β,γ-unsaturated α-keto esters

New Journal of Chemistry, Год журнала: 2024, Номер 48(4), С. 1688 - 1695

Опубликована: Янв. 1, 2024

This work diversified the Py-2NO ligand library recently developed by our group and further expanded application of chiral ligands in asymmetric catalysis.

Язык: Английский

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Recent advances in the synthesis of pyrrolo[1,2-a]indoles and their derivatives

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(35), С. 7544 - 7574

Опубликована: Янв. 1, 2021

This review focuses on recent developments in the synthesis of pyrrolo[1,2- a ]indole derivatives. The mechanism, factors affecting yield and selectivity product, application to bioactive molecules are explained.

Язык: Английский

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Chiral Phenol‐2NO Ligand Cooperation with Achiral Organic Base in the Zn(II)‐Catalyzed Asymmetric Alkylation Reaction of Indoles

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(13), С. 1474 - 1480

Опубликована: Март 1, 2024

Comprehensive Summary The privileged C 2 ‐symmetric rigid phenol‐type ligand is more attractive but challenging in asymmetric catalysis. Herein, we designed and synthesized a class of rigid‐featured chiral tridentate Phenol‐2NO ligands, that incorporate the advantages both phenol skeleton pyrroloimidazolone‐based N ‐oxide moiety, from readily available L ‐prolinamides operationally simple two steps up to 44% overall yield. More importantly, using an achiral quinoline derivative as additive, newly developed could serve anioic upon deprotonative activation coordinate Zn(II) form highly enantioselective catalyst for Michael‐type Friedel‐Crafts alkylation reaction indoles with 2,3‐dioxopyrrolidines. Excellent yields (up 90%) high enantioselectivities 99% ee) are obtained wide range substrates under mild conditions. Experiments DFT calculations revealed mechanism origins enantioselectivity. This also represented first ligand/metal complex by organic base additive

Язык: Английский

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Visible-light-induced cascade sulfonylation/cyclization of N-propargylindoles with aryldiazonium tetrafluoroborates via the insertion of sulfur dioxide

Organic & Biomolecular Chemistry, Год журнала: 2019, Номер 17(47), С. 10020 - 10029

Опубликована: Янв. 1, 2019

A simple and efficient visible-light-catalyzed cascade sulfonylation/cyclization of N-propargylindoles with K₂S₂O₅ aryldiazonium tetrafluoroborates for the construction 2-sulfonyl-substituted 9H-pyrrolo[1,2-a]indoles is developed.

Язык: Английский

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An unexpected cascade reaction of 3-hydroxyoxindoles with coumarin-3-carboxylates to construct 2,3-dihydrobenzofuran spirooxindoles

Chemical Communications, Год журнала: 2019, Номер 55(91), С. 13681 - 13684

Опубликована: Янв. 1, 2019

An unexpected Michael addition-inspired ring-opening/closure cascade reaction of 3-hydroxyoxindoles with coumarin-3-carboxylates was developed.

Язык: Английский

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Chalcone-Based Pyridinium Salts and Their Diastereoselective Dearomatization To Access Bibridged Benzoazepines

Organic Letters, Год журнала: 2020, Номер 22(3), С. 873 - 878

Опубликована: Янв. 9, 2020

New chalcone-based pyridinium salts have been successfully exploited, which could smoothly participate in the highly diastereoselective dearomatization with binucleophilic enaminones by taking advantage of their multiple reactive sites to construct bibridged benzoazepines up 89% yields. The key success was skillful and unprecedented C-3 functionalization new salts. This work not only provides a kind novel salt synthon but also achieves first complex challenging high synthetic efficiency.

Язык: Английский

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A short review on the synthesis of pyrrolo[3,4-c]coumarins an isolamellarin-B scaffolds

Synthetic Communications, Год журнала: 2022, Номер 52(21), С. 1999 - 2018

Опубликована: Сен. 7, 2022

This review presents a vast body of literature on various synthetic methodology, biological, and fluorescence activities pyrrolo[3,4‑c]coumarins as published during the last 20–30 years. Synthesized have been reported in by construction either pyrrole, indole, or both rings via different methodology including metal-catalyzed reactions, green reaction protocols starting from readily accessible substrates.

Язык: Английский

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Visible light photocatalytic asymmetric synthesis of pyrrolo[1,2-a]indoles via intermolecular [3+2] cycloaddition

Chemical Communications, Год журнала: 2019, Номер 55(75), С. 11303 - 11306

Опубликована: Янв. 1, 2019

The intermolecular diastereoselective and enantioselective synthesis of pyrrolo[1,2-a]indoles is developed through a [3+2] cycloaddition between silyl-indole derivatives α,β-unsaturated N-acyl oxazolidinones by merging photocatalysis Lewis acid catalysis.

Язык: Английский

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Access to 4-Alkenylated Coumarins via Ruthenium-Catalyzed Olefinic C–H Alkenylation of Coumarins with Modifiable and Removable Directing Groups

The Journal of Organic Chemistry, Год журнала: 2020, Номер 85(15), С. 9514 - 9524

Опубликована: Июнь 9, 2020

The ruthenium-catalyzed activation of the C4 position coumarins for coupling with acrylates was described using modifiable ketone as a directing group. alkenylation reaction provided direct approach to prepare previously inaccessible 4-alkenylated operational simplicity and high atom-economy. This protocol also worked well coumarin-3-carboxylic acids unveil rare instance tandem alkenylation/decarboxylation reaction. potential value this further highlighted by efficient synthesis several heterocyclic fused coumarin derivatives.

Язык: Английский

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