An un-forgotten classic: the nitro-Mannich reaction between nitrones and silyl nitronates catalysed by B(C6F5)3

Guerzoni, Michael G.; van Ingen, Yara; Babaahmadi, Rasool; Wirth, Thomas; Richards, Emma; Melen, Rebecca L.

doi:10.1039/d3sc05672d

Chem. Sci.

2024

DOI: 10.1039/d3sc05672d

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An un-forgotten classic: the nitro-Mannich reaction between nitrones and silyl nitronates catalysed by B(C₆F₅)₃

Michael G. Guerzoni,

Yara van Ingen,

Rasool Babaahmadi

et al.

Abstract: Herein we report the B(C6F5)3-catalysed nitro-Mannich reaction between nitrones and silyl nitronates, affording silyl-protected α-nitro hydroxylamines with yields up to 99% and diastereoselectivities up to 99:1. Crucially, the obtained products...

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Cited by 2 publications

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π‐Conjugation as a Direct Estimate of Lewis Acidity

González‐Pinardo,

Fernández

2024

Chemistry An Asian Journal

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A computational approach to directly estimate the relative acidity of a given Lewis acid is presented. This approach is based on the strength of the π‐conjugation in trans‐crotonaldehyde‐Lewis acid complexes, the species used in the well‐known Childs’ Lewis acidity scale. It is found that the π‐conjugative strength values given by the Energy Decomposition Analysis – Natural Orbital for Chemical Valence method strongly correlate not only with the variation of the bond lengths in the system, which are greatly affected by the nature of the Lewis acid but also with the downfield shifts experienced by the different nuclei of the conjugated system upon binding to the Lewis acid. These strong correlations indicate that the (easy‐to‐compute) π‐conjugation energies can be used as an alternative Lewis acidity scale.

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π‐Conjugation as a Direct Estimate of Lewis Acidity

González‐Pinardo,

Fernández

2024

Chemistry An Asian Journal

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Hydroxylamine‐O‐Sulfonic Acid (HOSA): A Recent Synthetic Overview

Kumar,

Divedi,

Chandra

et al. 2024

ChemistrySelect

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Hydroxylamine‐O‐sulfonic acid has been used as a versatile nitrogen source in synthetic organic chemistry. It has dual function and utilized both as a nucleophile and an electrophile during different synthetic transformations. This reagent is stable and easy to handle in both aqueous and organic solvents. It can be used with different functional groups under mild reaction conditions, making its widely applicable for constructing complex molecules. It has been utilized for various applications such as agrochemicals, pharmaceuticals, and polymer industries in the formation of S−N, C−N, O−N, and N−N bonds, as well as for efficient cyclization reactions under metal‐free conditions with excellent stereo– and regioselectivity. The present review provides a brief overview of all the advancements made in the past two decades using hydroxylamine‐O‐sulfonic acid as a nitrogen source.

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An un-forgotten classic: the nitro-Mannich reaction between nitrones and silyl nitronates catalysed by B(C₆F₅)₃

Abstract: Herein we report the B(C6F5)3-catalysed nitro-Mannich reaction between nitrones and silyl nitronates, affording silyl-protected α-nitro hydroxylamines with yields up to 99% and diastereoselectivities up to 99:1. Crucially, the obtained products...

Cited by 2 publications

References 47 publications

π‐Conjugation as a Direct Estimate of Lewis Acidity

π‐Conjugation as a Direct Estimate of Lewis Acidity

Hydroxylamine‐O‐Sulfonic Acid (HOSA): A Recent Synthetic Overview

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