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

Kumar,

Divedi,

Chandra

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

show abstract

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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 1 publication

References 47 publications

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

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

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