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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| Veröffentlicht in: | Chemical science (Cambridge) 2024-02, Vol.15 (7), p.2648-2654 |
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| creator | Guerzoni, Michael G van Ingen, Yara Babaahmadi, Rasool Wirth, Thomas Richards, Emma Melen, Rebecca L |
| description | 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. |
| doi_str_mv | 10.1039/d3sc05672d |
| format | Article |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| subjects | Chemistry Diamines Lewis acid Organic compounds Substrates |
| title | An un-forgotten classic: the nitro-Mannich reaction between nitrones and silyl nitronates catalysed by B(C 6 F 5 ) 3 |
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