An un-forgotten classic: the nitro-Mannich reaction between nitrones and silyl nitronates catalysed by B(C6F5)3
Michael G Guerzoni1, Yara van Ingen1, Rasool Babaahmadi1
1Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Translational Research Hub Maindy Road, Cathays Cardiff CF24 4HQ Cymru/Wales UK RichardsE10@cardiff.ac.uk MelenR@cardiff.ac.uk.
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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