Stereoselective synthesis and applications of spirocyclic oxindoles

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(5), P. 1026 - 1084

Published: Jan. 1, 2021

This review summaries recent synthetic developments towards spirocyclic oxindoles and applications as valuable medicinal targets.

Language: Английский

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Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.

Language: Английский

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Recent progress in the application of iodonium ylides in organic synthesis

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(24), P. 6999 - 7015

Published: Jan. 1, 2022

This review summarizes the recent advances in synthetic application of iodonium ylides covering 2017 to 2022.

Language: Английский

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A new dehydrogenative [4 + 1] annulation between para-quinone methides (p-QMs) and iodonium ylides for the synthesis of 2,3-dihydrobenzofurans

Organic Chemistry Frontiers, Journal Year: 2018, Volume and Issue: 5(23), P. 3483 - 3487

Published: Jan. 1, 2018

A new dehydrogenative [4 + 1] annulation of para-quinone methides (p-QMs) with acyclic and cyclic iodonium ylides has been established, delivering a variety functionalized 2,3-dihydrobenzofurans the retention quinone methide unit in generally good yields.

Language: Английский

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Blue LED Irradiation of Iodonium Ylides Gives Diradical Intermediates for Efficient Metal‐free Cyclopropanation with Alkenes

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(47), P. 16959 - 16965

Published: Sept. 5, 2019

A facile and highly chemoselective synthesis of doubly activated cyclopropanes is reported where mixtures alkenes β-dicarbonyl-derived iodonium ylides are irradiated with light from blue LEDs. This metal-free gives in yields up to 96 %, operative cyclic acyclic ylides, proceeds a variety electronically-diverse alkenes. Computational analysis explains the high selectivity observed, which derives exclusive HOMO LUMO excitation, instead free carbene generation. The procedure operationally simple, uses no photocatalyst, provides access one step important building blocks for complex molecule synthesis.

Language: Английский

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Access to highly enantioselective and diastereoselective spirooxindole dihydrofuran fused pyrazolones

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(9), P. 1794 - 1799

Published: Jan. 1, 2020

Access to highly enantioselective and diastereoselective spirooxindole dihydrofuran fused pyrazolones from MBH-carbonates pyrazole 4,5-diones.

Language: Английский

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Oxidative Reactions Mediated by Hypervalent Iodine Reagents

Elsevier eBooks, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

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Ag(I)-Catalyzed Tandem Reaction of Conjugated Ene-yne-ketones in the Presence of PhI(OAc)₂ and Triethylamine: Synthesis of 2-Alkenylfurans

Organic Letters, Journal Year: 2019, Volume and Issue: 21(7), P. 2416 - 2420

Published: March 26, 2019

Silver-catalyzed tandem cyclization–elimination reactions of conjugated ene-yne-ketones in PhI(OAc)2/triethylamine system lead to the formation 2-alkenylfurans. 2-Furylsilver carbene and phenyliodonium ylide are proposed as key intermediates these transformations.

Language: Английский

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Green Protocols for the Synthesis of 3,3’-spirooxindoles – 2016- mid 2019

Current Green Chemistry, Journal Year: 2019, Volume and Issue: 6(3), P. 210 - 225

Published: Dec. 18, 2019

Spirooxindoles, particularly 3,3’-spirooxindoles constitute a privileged structural scaffold owing to the intensive biological activities which they possess. Because of this over last twenty years, large number methods were devised for their synthesis and some these molecules have entered pre-clinical trials. Of late, spirooxindole using green protocols developed rapidly. Reactions based on multicomponent strategies non-catalytic / biocatalytic pathways those done in aqueous media been largely employed 3,3’- spirooxindoles. This review focusses via covers literature from 2016 onwards (2016 - mid 2019); same topic has appeared 2016. The discussed here include reactions media, strategies, alternate solvents photocatalysis.

Language: Английский

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Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(12), P. 7724 - 7735

Published: Jan. 27, 2023

The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1-nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-to-good isolated yields (15-69%) excellent stereochemical outcomes. synthetic utility protocol was exemplified on a set additional transformations corresponding spirooxindole compounds.

Language: Английский

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