Rh(III)-Catalyzed [4 + 1] Annulation of Sulfoximines with Maleimides: Access to Benzoisothiazole Spiropyrrolidinediones DOI
Liansheng Liu, Yiying Liu, Shan Li

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3626 - 3635

Published: Feb. 27, 2023

Rh(III)-catalyzed synthesis of benzoisothiazole spiropyrrolidinediones using sulfoximine as a directing group under C–H activation and [4 + 1] annulation strategy with maleimides coupling partner is reported. The cyclization reaction was compatible various substituted maleimides. deuterium-labeling studies were performed to investigate the mechanism reaction.

Language: Английский

Planar chiral arene ruthenium complexes derived from R-carvone DOI
Mikhail A. Boym, Roman A. Pototskiy, Evgeniya Podyacheva

et al.

Dalton Transactions, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Natural R -carvone was converted into ruthenium complexes with planar-chiral arene ligands. Similar to the classical [(cymene)RuCl 2 ] complex, they catalyse C–H activation reactions, albeit low stereoselectivity.

Language: Английский

Citations

0

Synthesis of Sulfoximines and Cyclic Sulfoximines DOI
Qingle Zeng,

Alex Adonis Nking’wa

Published: Jan. 1, 2025

Language: Английский

Citations

0

Recent Advances in Asymmetric Synthesis of Chiral-at-Sulfur Sulfoximines DOI
Muhammad Suleman,

Tianming Huang,

Tao Zhou

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 5511 - 5530

Published: March 19, 2025

Language: Английский

Citations

0

Allylic Acetal as 3C Synthon in Rh(III)-Catalyzed Divergent C–H Activation/[4 + 3] Annulation: Easy Access to Benzodiazepines DOI
Mingming Hu, Chao Pi, Yangjie Wu

et al.

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

Published: April 2, 2025

A concise synthesis of benzodiazepines via Rh(III) catalyzed C-H activation/ [4 + 3] annulation easily available 1-arylpyrazolidinones with allylic acetal has been developed. The was employed as a novel 3C synthon in this transformation. Benzodiazepines were built under mild reaction conditions high efficiency and chemoselectivity. atom-economy accessible substrates reveal potential application.

Language: Английский

Citations

0

Unanticipated Three-Component Cascade and Sequential Cyclization: Highly Diastereoselective Synthesis of Polyfunctionalized Cyclohexanes DOI

Qing He,

Rui Zhou, Bin Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 11, 2025

Herein, we reported a DBU-catalyzed cascade and sequential [1 + 2 3] annulation of malononitrile with α,β-unsaturated ketones to access polyfunctionalized cyclohexanes high yield excellent diastereoselectivity (>93% yield, >19:1 dr). Intriguingly, this appears be the new strategy for using either as 2C or 3C synthon react dinucleophile 1C construct six-membered carbocycles in one-pot manner. In addition, these synthesized compounds suppressed growth phytopathogenic fungi vitro. Among them, compound 3l exhibited broad antifungal activity, which possesses potential an agricultural agent.

Language: Английский

Citations

0

Modular Synthesis of 1,2-Benzothiazines and 1,2-Benzothiazine 1-Imines via Palladium-Catalyzed C–H/C–C Activation Reactions DOI
Yifan Ren,

Lisha Mo,

Yali Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3345 - 3358

Published: Feb. 19, 2024

In this study, a modular approach toward cyclic sulfoximines and sulfondiimines via palladium-catalyzed intramolecular C-H/C-C activation reactions was reported. Various 1,2-benzothiazines including bicyclic, tricyclic, highly fused ones, ones of the seven-membered ring, along with 1,2-benzothiazine 1-imines were accessed in good yields. KIE experiment demonstrated that C-H bond cleavage at position

Language: Английский

Citations

3

Kinetic Resolution of Sulfoximines via Asymmetric Organocatalyzed Formation of Benzothiadiazine-1-oxides DOI

Mengyao Tang,

Mengyao Yuan,

Shibin Hong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1914 - 1919

Published: Feb. 29, 2024

A catalytic kinetic resolution of sulfoximines has been developed through chiral phosphoric acid-catalyzed intramolecular dehydrative cyclizations. variety racemic bearing an ortho-amidophenyl moiety underwent asymmetric cyclizations using this method, yielding both the recovered and benzothiadiazine-1-oxide products with good to high enantioselectivities (with s-factor up 61). The diverse derivatizations into a wide range S-stereogenic center-containing S,N-heterocycles have demonstrated value method.

Language: Английский

Citations

3

Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp3)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development DOI
Weijie Chen, Huiying Xu,

Fu‐Xiaomin Liu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(20)

Published: March 19, 2024

Abstract Herein, multiple types of chiral Os(II) complexes have been designed to address the appealing yet challenging asymmetric C(sp 3 )−H functionalization, among which Os(II)/Salox species is found be most efficient for precise stereocontrol in realizing amidation. As exemplified by enantioenriched pyrrolidinone synthesis, such tailored catalyst efficiently enables an intramolecular site‐/enantioselective amidation γ‐position dioxazolone substrates, benzyl, propargyl and allyl groups bearing various substituted forms are well compatible, affording corresponding γ‐lactam products with good er values (up 99 : 1) diverse functionality (>35 examples). The unique performance advantage developed system terms catalytic energy profile induction has further clarified integrated experimental computational studies.

Language: Английский

Citations

3

Pd-Catalyzed Atroposelective C–H Olefination: Diverse Synthesis of Axially Chiral Biaryl-2-carboxylic Acids DOI

Ao‐Lian Jiang,

Gang Zhou,

Bo‐Yang Jiang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5670 - 5675

Published: June 26, 2024

Axially chiral carboxylic acids are important motifs in catalysts and ligands. We herein reported the synthesis of axially via Pd(II)-catalyzed atroposelective C-H olefination using acid as native directing group. A broad range axial biaryl-2-carboxylic were synthesized good yields with high enantioselectivities (up to 84% yield 99% ee). Gram-scale reaction further transformation reactions also provide a platform for synthetic applications this method.

Language: Английский

Citations

3

Half-Sandwich d6-Metal (CoIII, RhIII, IrIII, RuII)-Catalyzed Enantioselective C–H Activation DOI Creative Commons
Pu‐Fan Qian, Jun-Yi Li, Yibo Zhou

et al.

SynOpen, Journal Year: 2023, Volume and Issue: 07(04), P. 466 - 485

Published: Sept. 6, 2023

Abstract Transition-metal-catalyzed enantioselective C–H activation provides a straightforward strategy to synthesize chiral molecules from readily available sources. In this graphical review, we summarize the progress on half-sandwich d6-metal (CoIII, RhIII, IrIII, RuII)-catalyzed functionalization reactions. The review is categorized according type of metal catalyst and ligand employed. Representative enantio-determining models catalytic cycles are presented.

Language: Английский

Citations

7