An un-forgotten classic: the nitro-Mannich reaction between nitrones and silyl nitronates catalysed by B(C 6 F 5 ) 3

Herein we report the B(C F ) -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 can be converted into 1,2-diamines under simple reduc...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2024-02, Vol.15 (7), p.2648-2654
Main Authors: Guerzoni, Michael G, van Ingen, Yara, Babaahmadi, Rasool, Wirth, Thomas, Richards, Emma, Melen, Rebecca L
Format: Article
Language:English
Subjects:
Chemistry
Diamines
Lewis acid
Organic compounds
Substrates
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Summary:Herein we report the B(C F ) -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 can be converted into 1,2-diamines under simple reductive conditions. This work provides a new orthogonal method to the existing routes for the instalment of a nitro moiety under Lewis acid catalysed conditions, and expands the state-of-the-art substrate scope with respect to the silyl nitronates.
ISSN:2041-6520
2041-6539
DOI:10.1039/d3sc05672d