Recent advances in the (3+2) cycloaddition of azomethine ylide

Das, Tapas K.; Jana, Rathin; Dubey, Sapana; Pal, Anit; Roy, S.C.; Sasmal, Souvik; Tamrakar, Aashi

doi:10.1039/d3nj01018j

Cited by 17 publications

(11 citation statements)

References 160 publications

(88 reference statements)

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“…Especially, asymmetric [3+2] cycloaddition is considered one of the trickiest approaches in synthetic organic chemistry. 57,58 In 2018, Wang and Tang realized the synthesis of optically pure benzofuroindolines 3 via the enantioselective [3+2] annulation of p -benzoquinone 1 with indoles 2 . 59 The transformation was carried out in dichloromethane with the aid of a BOX ligand copper( ii ) hydrate complex (Catalyst L1 ) and 4 Å molecular sieves.…”

Section: Synthesis Of Fused Frameworkmentioning

confidence: 99%

Annulations involving p-benzoquinones: stereoselective synthesis of fused, spiro and bridged molecules

Das

2024

New J. Chem.

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Section: Synthesis Of Fused Frameworkmentioning

confidence: 99%

Annulations involving p-benzoquinones: stereoselective synthesis of fused, spiro and bridged molecules

Das

2024

New J. Chem.

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“…Azomethine ylides have been employed in many elegant applications for the preparation of a pyrrolidine nucleus and for the productions of natural products, drugs, and agrochemical compounds [42].…”

Section: Azomethyne Ylidesmentioning

confidence: 99%

Density Functional Theory Calculations: A Useful Tool to Investigate Mechanisms of 1,3-Dipolar Cycloaddition Reactions

Chiacchio,

Legnani

2024

IJMS

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The present review contains a representative sampling of mechanistic studies, which have appeared in the literature in the last 5 years, on 1,3-dipolar cycloaddition reactions, using DFT calculations. Attention is focused on the mechanistic insights into 1,3-dipoles of propargyl/allenyl type and allyl type such as aza-ylides, nitrile oxides and azomethyne ylides and nitrones, respectively. The important role played by various metal–chiral–ligand complexes and the use of chiral eductors in promoting the site-, regio-, diastereo- and enatioselectivity of the reaction are also outlined.

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“…The three-component domino reaction of amino acids with ketones and activated alkenes is a powerful method of synthesis of various substituted pyrrolidines, including highly strained molecules [29][30][31]. This reaction was used to prepare highly strained, stable nitroxides with β-hydrogen [32].…”

Section: Introductionmentioning

confidence: 99%

2,5-Di-tert-butyl-2,5-diethylpyrrolidine-1-oxyls: Where Is a Reasonable Limit of Sterical Loading for Higher Resistance to Reduction?

Zhurko,

Dobrynin,

Glazachev

et al. 2024

Molecules

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The pyrrolidine nitroxides with four bulky alkyl substituents adjacent to the N–O∙ group demonstrate very high resistance to reduction with biogenic antioxidants and enzymatic systems. This makes them valuable molecular tools for studying the structure and functions of biomolecules directly in a living cell and for functional EPR and NMR tomography in vivo. The first example of highly strained pyrrolidine nitroxides with both ethyl and tert-butyl groups at each of the α-carbon atoms of the nitroxide moiety with cis-configuration of the tert-butyl groups was prepared using a three-component domino reaction of tert-leucine and 2,2-dimethylpentan-3-one with dimethyl fumarate with subsequent conversion of the resulting strained pyrrolidine into 1-pyrroline-1-oxide and addition of EtLi. The nitroxide has demonstrated unexpectedly fast reduction with ascorbate, the rate constant k2 = (2.0 ± 0.1) × 10−3 M−1s−1. This effect was explained by destabilization of the planar nitroxide moiety due to repulsion with the two neighboring tert-butyl groups cis to each other.

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Recent advances in the (3+2) cycloaddition of azomethine ylide

Abstract: Nitrogen-containing heterocyclic compounds are some of the most significant that are produced artificially or naturally. These heterocyclic rings are virtually always present in biological systems, from the smallest eukaryotes to...

Cited by 17 publications

References 160 publications

Annulations involving p-benzoquinones: stereoselective synthesis of fused, spiro and bridged molecules

Annulations involving p-benzoquinones: stereoselective synthesis of fused, spiro and bridged molecules

Density Functional Theory Calculations: A Useful Tool to Investigate Mechanisms of 1,3-Dipolar Cycloaddition Reactions

2,5-Di-tert-butyl-2,5-diethylpyrrolidine-1-oxyls: Where Is a Reasonable Limit of Sterical Loading for Higher Resistance to Reduction?

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