Palladium‐Catalyzed Umpolung Allylation of Isatin‐Derived Azomethine Imines with Vinylcyclopropanes DOI
Yue Wang,

Xingfu Wei,

Jingping Qü

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(45)

Published: Aug. 22, 2024

Abstract A Pd‐catalyzed umpolung allylation of isatin‐derived azomethine imines with vinyl cyclopropanes was disclosed. This protocol provides an efficient and atom‐economic approach to access array structurally interesting allylic aminooxindole derivatives in good yields linear‐selectivities (up 95 % yield). Further product derivatization asymmetric catalytic studies proved the practicability reaction potential application.

Language: Английский

Synthesis of Diverse 4‐Pyrrolin‐2‐ones by Electrochemically Induced Dehydrogenative Regioselective Cyclization of 3‐Aza‐1,5‐dienes and 1,3‐Dicarbonyl Compounds DOI
Xing Ji,

Run He,

Lou Shi

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(11)

Published: Jan. 20, 2024

Abstract A practical and mild electrochemical dehydrogenative regioselective cyclization method has been established for the synthesis of 4‐pyrrolin‐2‐ones using 3‐aza‐1,5‐dienes 1,3‐dicarbonyl compounds as substrates. This protocol is catalyst‐free, metal‐free, does not require oxidizing agents. It exhibits wide substrate compatibility can be easily scaled up to gram scale.

Language: Английский

Citations

9

Ruthenium-Catalyzed Difunctionalization of Vinyl Cyclopropanes for Double m-C(sp2)–H/C-5(sp3)–H Functionalization DOI

Yu‐Yong Luan,

Jinye Li,

Wei‐Yu Shi

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3213 - 3217

Published: April 4, 2024

With in-depth research on 1,2-difunctionalization, remote difunctionalization has garnered widespread attention for achieving multifunctionality. Herein, we report a strategy under mild conditions. This exhibited good substrate suitability and functional group tolerance. In addition, the significance of this method is further evidenced by its successful application in scaling up conducting additional transformations target compounds. Mechanistic studies showed that radical might be involved process.

Language: Английский

Citations

6

Catalytic Asymmetric Ring Opening Reactions of Vinylcyclopropanes DOI

Amit Singh Adhikari,

Nilanjana Majumdar

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(19)

Published: Jan. 11, 2024

Abstract Vinylcyclopropanes (VCPs) are important building blocks with multifaceted reactivity. Catalytic asymmetric ring opening of vinylcyclopropanes is a highly efficient process to access valuable chiral molecules diverse functionalities that can be further functionalized for series synthetic purposes. VCPs very well‐known substrates cycloaddition reactions and this chemistry has been widely explored. On the contrary, despite enormous potential, development new innovative strategies catalytic, somewhat underdeveloped. Recently, several significant examples have emerged in literature various both activated unactivated involve transition metal catalysis. These developments relevant additions vinylcyclopropane chemistry. In review, we aim summarize all catalytic transformations reported till date provide comprehensive analysis these research outcomes.

Language: Английский

Citations

5

Asymmetric Amination of Unstrained C(sp3)–C(sp3) Bonds DOI Creative Commons
Yang Liu,

Ye‐Wei Chen,

Yuanxiang Yang

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(43), P. 29857 - 29864

Published: Oct. 16, 2024

The asymmetric functionalization of unstrained C(sp3)–C(sp3) bonds could be a powerful strategy to stereoselectively reconstruct the backbone an organic compound, but such reactions are rare. Although allylic substitutions have been used frequently construct C–C by cleavage more reactive C–X (X is usually O atom ester) transition metals, reverse process that involves replacement bond with C–heteroatom rare and generally considered thermodynamically unfavorable. We show unstrained, inert σ can converted C–N via designed solubility-control strategy, which makes unfavorable possible. amination occurs range amine nucleophiles cleaves multiple classes alkyl in good yields high enantioselectivity. A novel resolution also reported transforms racemic amines corresponding optically active sequential conversion back bond. Mechanistic studies formation rate-limiting step driven low solubility salt formed from cleaved group nonpolar solvent.

Language: Английский

Citations

3

Iridium/Acid Dual-Catalyzed Enantioselective Aza-ene-type Allylic Alkylation of Nitro Ketene Aminals with Racemic Allylic Alcohols DOI

Diancong Chen,

Man Zhang, Dongxu Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(2), P. 508 - 513

Published: Jan. 5, 2024

The enantioselective allylic alkylation of nitro ketene aminals with racemic alcohols was realized by iridium/acid dual catalysis. An allyl group installed on the α-position in a branched-selective manner high efficiency excellent enantioselectivities (93–99% ee). protocol applied to late-stage modification neonicotinoid insecticides, which directly furnished novel analogue good insecticidal activity against Aphis craccivora (LC50 = 6.40 mg/L). On basis control experiment, an aza-ene-type reaction mechanism proposed.

Language: Английский

Citations

3

Enantioselective synthesis of 2-amino-4H-chromene derivatives with antifungal activities on phytopathogenic fungi DOI
Man Zhang,

Yifan Ru,

Shilin Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(13), P. 3692 - 3699

Published: Jan. 1, 2024

An Ir-catalyzed enantioselective cascade allylation/cyclization reaction of 2-(1-hydroxyallyl)phenols was developed, affording antifungal 2-amino-4 H -chromene derivatives with good to excellent enantioselectivities.

Language: Английский

Citations

1

Electrochemical 1,5-chlorosulfonylation and 1,5-hydrosulfonylation of vinylcyclopropanes DOI
Xin Zhang, Wei Li,

Yuxiang Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5564 - 5572

Published: Jan. 1, 2024

This study reports the electrochemical reaction of vinylcyclopropanes with sulfonyl chlorides, resulting in 1,5-hydrosulfonylation and 1,5-chlorosulfonylation.

Language: Английский

Citations

1

Ir/Brønsted acid dual-catalyzed asymmetric synthesis of bisbenzannulated spiroketals and spiroaminals from isochroman ketals DOI
Yang Chen, Hui Yan, Hanliang Zheng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5831 - 5840

Published: Jan. 1, 2024

An Ir/Brønsted acid dual-catalyzed asymmetric cascade reaction of 2-(1-hydroxyallyl)phenols with isochroman ketals was developed, affording antifungal spiroketals high enantioselectivities.

Language: Английский

Citations

1

DFT Study on the Mechanism of Phosphine-Catalyzed Ring-Opening Reaction of Cyclopropyl Ketone DOI
Xiaohan Yu, Yang Wang

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

In the present study, mechanism, origin of chemoselectivity, and substituent effects phosphine-catalyzed ring-opening reaction cyclopropyl ketone have been investigated using DFT method. Multiple pathways, including formation hydrofluorenone, Cloke-Wilson product, cyclopenta-fused were studied compared. The computational results show that pathway for hydrofluorenone is most favorable one, which involves four processes: nucleophilic substitution to open three-membered ring, an intramolecular Michael addition enolate intermediate, [1,5]-proton transfer give ylide, Wittig deliver final product. For disclosing structural analysis local reactivity index performed. Moreover, also considered QTAIM analysis. current study would provide useful insights understanding chemoselective reactions.

Language: Английский

Citations

1

Evolution of a ‘privileged’ P-alkene ligand: added planar chirality beats BINOL axial chirality in catalytic asymmetric C–C bond formation DOI

Luisa Leinauer,

Giorgio Parla,

Julian Messelbeger

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(97), P. 14451 - 14454

Published: Jan. 1, 2023

Alkene planar chirality is introduced in the 'privileged' P-alkene phosphoramidite ligand 1. The resulting diastereomeric ligands (pR,R)-5 and (pS,R)-5 form optically pure complexes of Rh(I) Pd(II), which catalyze conjugate additions boron C-nucleophiles to enones allylic alkylations, respectively. In Rh-catalyzed reaction, alkene exerts absolute enantiocontrol over potent BINOL auxiliary.

Language: Английский

Citations

1