Oxidative [3+2] Annulation of Pyridinium Salts with gem‐Difluoroalkenes: Synthesis of 2‐Fluoroindolizines DOI

Li‐Miao Yang,

You‐Ya Zhang,

Jing‐Tong Deng

et al.

Asian Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 10(7), P. 1679 - 1682

Published: April 9, 2021

Abstract An oxidative [3+2] annulation of pyridinium salts with gem ‐difluoroalkenes for the synthesis highly substituted 2‐fluoroindolizines has been developed. Using DBU as base, a broad range multisubstituted were prepared in good to excellent yields under mild conditions, and many useful functional groups can be tolerated.

Language: Английский

Stereospecific Synthesis of Unprotected, α,β-Disubstituted Tryptamines and Phenethylamines from 1,2-Disubstituted Alkenes via a One-Pot Reaction Sequence DOI
Duc Chu, Jonathan A. Ellman

Organic Letters, Journal Year: 2023, Volume and Issue: 25(20), P. 3654 - 3658

Published: May 12, 2023

Unprotected, α,β-disubstituted tryptamines and phenethylamines are obtained by a one-pot, metal-free sequence that proceeds the in situ formation of aziridinium salts followed Friedel–Crafts reaction with electron-rich (hetero)arenes. Both steps facilitated hexafluoroisopropanol as solvent. The one-pot was effective for diversely substituted indoles 1,3,5-trimethoxybenzene, cyclic acyclic alkenes, proceeded stereospecific fashion both (E)- (Z)-1,2-disubstituted alkenes. Moreover, morpholine addition to an salt provided diamine.

Language: Английский

Citations

14
Catalytic Synthesis of β‐(Hetero)arylethylamines: Modern Strategies and Advances DOI Creative Commons
Valentyn Pozhydaiev, Cyprien Muller, Joseph Moran

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(41)

Published: Aug. 21, 2023

Abstract β‐(Hetero)arylethylamines appear in a myriad of pharmaceuticals due to their broad spectrum biological properties, making them prime candidates for drug discovery. Conventional methods preparation often require engineered substrates that limit the flexibility synthetic routes and diversity compounds can be accessed. Consequently, provide rapid versatile access those scaffolds remain limited. To overcome these challenges, chemists have designed innovative modular strategies β‐(hetero)arylethylamine motif, paving way more extensive use future pharmaceuticals. This review outlines recent progresses synthesis (hetero)arylethylamines emphasizes how innovations enabled new levels molecular complexity, selectivity, practicality.

Language: Английский

Citations

13
Nickel-Catalyzed Enantioselective C(sp3)–C(sp3) Cross-Electrophile Coupling of N-Sulfonyl Styrenyl Aziridines with Alkyl Bromides DOI
Yun Lan,

Qiaoying Han,

Pingyong Liao

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(37), P. 25426 - 25432

Published: Sept. 4, 2024

Herein, we report the first example of a highly enantioselective alkylative aziridine ring opening. Under catalysis chiral nickel/pyridine-imidazoline complex, asymmetric C(sp

Language: Английский

Citations

5
A Scaffold‐Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides DOI Creative Commons
Stefan Zimmermann,

Mohammad Akbarzadeh,

Felix Otte

et al.

Chemistry - A European Journal, Journal Year: 2019, Volume and Issue: 25(68), P. 15498 - 15503

Published: Sept. 13, 2019

Abstract A “branching–folding” synthetic strategy that affords a range of diverse cyclic benzo‐sulfonamide scaffolds is presented. Whereas different annulation reactions on common ketimine substrates build the branching phase scaffold synthesis, hydrogenative ring‐expansion method, facilitated by an increase ring‐strain during phase, led to sulfonamides bearing medium‐sized rings in folding pathway. Cell painting assay was successfully employed identify tubulin targeting as novel mitotic inhibitors.

Language: Английский

Citations

39
Catalytic Asymmetric Transformations of Racemic Aziridines DOI
Zhuo Chai

Synthesis, Journal Year: 2020, Volume and Issue: 52(12), P. 1738 - 1750

Published: March 16, 2020

The catalytic asymmetric ring-opening transformations of aziridines represent an important strategy for the construction various chiral nitrogen-containing molecular architectures. This short review covers progress achieved in transformation racemic aziridines, focusing on strategies employed each different type such aziridines. 1 Introduction 2 Reaction Racemic 2-Vinylaziridines 3 2-Alkylaziridines 3.1 Regiodivergent Parallel Kinetic Resolution 3.2 4 2-(Hetero)arylaziridines 4.1 4.2 Enantioconvergent Transformation 5 Donor–Acceptor-Type Aziridines 6 Conclusion and Outlook

Language: Английский

Citations

36
Enantioselective Synthesis of 3-Allylindolizines via Sequential Rh-Catalyzed Asymmetric Allylation and Tschitschibabin Reaction DOI
Ke Li, Changkun Li

Organic Letters, Journal Year: 2020, Volume and Issue: 22(24), P. 9456 - 9461

Published: Dec. 2, 2020

The first highly regio- and enantioselective synthesis of 3-allylindolizines has been developed by the sequential Rh-catalyzed asymmetric allylation Tschitschibabin reaction. Above 20:1 branch/linear ratio, up to a 96% yield 99% ee could be obtained with help tert-butyl-substituted chiral bisoxazolinephosphine ligand. In situ generated nucleophilic 2-alkylpyridinium ylides are utilized undergo alkylation reaction before cyclization.

Language: Английский

Citations

34
Catalytic Aminium Radical-Cation Salt (Magic Blue)-Initiated SN2-Type Nucleophilic Ring-Opening Transformations of Aziridines DOI

Bharat Singh,

Suraj Kashyap,

Shishir Singh

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2247 - 2263

Published: Feb. 7, 2024

A simple and atom economic protocol for the construction of C–X/C–C bonds via catalytic aminium radical-cation salt (Magic Blue)-initiated SN2-type nucleophilic ring-opening transformations racemic nonracemic aziridines with different hetero carbon nucleophiles to afford various amino ethers, thioethers, amines in up 99% yield, perfect enantiospecificity some substrates but reduced ee others (for aziridines), is developed. This salt-initiated, strategy, along cyclization protocols, employed synthesize biologically significant compounds.

Language: Английский

Citations

4
Palladium Catalysis Enabled Sequential C(sp3)–H/C–C Activation: Access to Vinyl γ-Lactams DOI

Madhab Barman,

Manmath Mishra,

Santu Mandal

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3722 - 3726

Published: April 28, 2024

A Pd(II)-catalyzed tandem reaction of aliphatic amides with vinylcyclopropanes (VCPs) was accomplished by merging C(sp3)–H and C–C activation. The VCP revealed alkenylation/cyclization, followed ring opening via cleavage, delivering vinyl γ-lactams (E)-selectivity. role ligands, site-selectivity, functional group diversity, mechanistic insight, synthetic utilities are important practical features.

Language: Английский

Citations

4
Dearomative Alkylation-Based Two-Step cis-Diastereoselective Synthesis of Indoline-2,3-Fused Chromans and Tetrahydropyrans DOI

Raju Chouhan,

Nandini Ray,

Nitish Nayan Gogoi

et al.

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

Published: Oct. 3, 2024

Herein, we describe a two-step,

Language: Английский

Citations

4
Electrochemical Ring Opening and [3 + 2] Cycloaddition of Aziridines: Access to 1,2-Bifunctionalized Products and Imidazolines DOI
Shiv Dutt,

Neelam Duhan,

Vikas Kale

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(4), P. 989 - 994

Published: Jan. 21, 2025

Herein, we report an electricity-driven activation of aziridine via direct anodic oxidation to give N-heterocycles and 1,2-bifunctionalized products by excluding any oxidant/reductant or metal catalyst. Many structurally modified aziridines were employed in the presence different nitriles. A large variety nucleophiles screened furnish chemoselectively O-alkylated C-alkylated products. Late-stage derivatization with natural medicinally active compounds has also been done. Remarkably, our strategy was found be a greener, sustainable, atom-economical approach (E-factor = ca. 0.8). Azetidine compatible protocol generated six-membered N-heterocycles. The detailed mechanistic study highlighted that reaction is driven generation radical cation followed SN2 nucleophilic attack.

Language: Английский

Citations

0