Silver-catalyzed synthesis of nitrogen heterocycles: recent advancements

Devi, P.; Neetha, Mohan; Anilkumar, Gopinathan

doi:10.1039/d3ob00277b

Cited by 11 publications

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References 97 publications

(98 reference statements)

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“…Here we present a novel and straightforward method for the enantioselective synthesis of a family of chiral α-disubstituted β-homoprolines, which allows one to afford the desired products in both enantiomeric forms, using readily available and cost-effective reagents and exploiting well-established and reliable synthetic transformations. Amidst the plethora of methodologies for the construction of nitrogen-containing heterocycles, 14 the addition of organometallic reagents to chiral sulfinimines, followed by the intramolecular cyclization of nitrogen on an opportunely positioned leaving group, appears to be particularly appealing. This strategy was originally pioneered by Ruano for the synthesis of optically pure 2-(1-hydroxybenzyl)piperidine and pyrrolidine 15a and later found broad application in the construction of chiral pyrrolidine scaffolds ( 5 ) from 4-halobutanal-derived chiral sulfinimines 4 ( Scheme 1 ).…”

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Stereoselective Synthesis of α-Disubstituted β-Homoprolines

Quintavalla,

Carboni,

Simeone

et al. 2023

Org. Lett.

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An efficient enantioselective synthesis of chiral α-disubstituted β-homoprolines was developed, starting with the stereodivergent allylation of chiral N-tert-butanesulfinyl imines derived from 4-bromobutanal with indium or zinc and using well-established and reliable synthetic transformations. This methodology allows the easy introduction of different substituents at the α-position of the pyrrolidine scaffold and is characterized by the possibility of switching the absolute configuration of the newly formed stereocenter either by changing the configuration of the tert-butanesufinamide chiral auxiliary or by using a different stereodivergent allylation protocol with the same auxiliary.

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confidence: 99%

Stereoselective Synthesis of α-Disubstituted β-Homoprolines

Quintavalla,

Carboni,

Simeone

et al. 2023

Org. Lett.

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Catalytic Asymmetric Cycloadditions of Cyclic Sulfamidate Imines: Straightforward Access to Chiral N‐Heterocycles

Park,

Hyun Kim

2024

Adv Synth Catal

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Chiral N‐heterocyclic compounds are key structures in natural compounds and pharmaceuticals, and they serve as essential building blocks of functional materials. Catalytic asymmetric cycloaddition reactions represent one of the most efficient synthetic strategies for constructing optically active heterocycles. Cyclic sulfamidate imines have recently come to be extensively studied and widely utilized in both organocatalytic and transition metal‐catalyzed asymmetric cycloadditions, where they have been shown to provide various N‐fused‐heterocycles and spiro‐cycles exhibiting high efficiencies with excellent stereoselectivities. This review highlights recent advancements in catalytic asymmetric cycloadditions of cyclic sulfamidate imines for the stereoselective synthesis of biologically active sulfamidate‐containing heterocycles since 2012 while focusing on the diverse reactivities of cyclic sulfamidate imines and the mechanisms of chiral induction in catalysis.

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Skeletal Editing of Isatins for Heterocycle Molecular Diversity

Zhang,

Feng

2024

The Chemical Record

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Isatins have been widely used in the preparation of a variety of heterocyclic compounds, where the skeletal editing of isatins has shown significant advantages for the construction of diverse heterocycles. This review highlights the progress made in the last decade (2013−2023) in the skeletal editing of the isatin scaffold. A series of ring expansion reactions for the construction of quinoline skeleton, quinolone skeleton, polycyclic quinazoline skeleton, medium‐sized ring skeleton, as well as a series of ring opening reactions for the generation of 2‐(azoly)aniline skeleton by the cleavage of C−C bond and C−N bond are highlighted. It is hoped that this review will provide some understanding of the chemical transformations of isatins and contribute to the further realization of its molecular diversity.

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Silver-catalyzed synthesis of nitrogen heterocycles: recent advancements

Abstract: Silver catalysis offers environmentally friendly and simple protocols to construct N-heterocycles. Inspired by its appeal, herein we have summarized developments in the silver-catalyzed synthesis of N-heterocycles since 2019.

Cited by 11 publications

References 97 publications

Stereoselective Synthesis of α-Disubstituted β-Homoprolines

Stereoselective Synthesis of α-Disubstituted β-Homoprolines

Catalytic Asymmetric Cycloadditions of Cyclic Sulfamidate Imines: Straightforward Access to Chiral N‐Heterocycles

Skeletal Editing of Isatins for Heterocycle Molecular Diversity

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