An un-forgotten classic: the nitro-Mannich reaction between nitrones and silyl nitronates catalysed by B(C6F5)3†
Michael G.
Guerzoni, 
a
Rasool
Babaahmadi,
a
Thomas
Wirth,
b
Emma
Richards
*ab
and
Rebecca L.
Melen
*a
a
Rasool
Babaahmadi,
a
Thomas
Wirth,
b
Emma
Richards
*ab
and
Rebecca L.
Melen
*a
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 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.
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