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 ORCID: https://orcid.org/0000-0002-8990-0667, Richards, Emma ORCID: https://orcid.org/0000-0001-6691-2377 and Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831 2024. An un-forgotten classic: the nitro-Mannich reaction between nitrones and silyl nitronates catalysed by B(C6F5)3 †. Chemical Science 15 (7) 10.1039/d3sc05672d

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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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Additional Information:	License information from Publisher: LICENSE 1: URL: http://creativecommons.org/licenses/by/3.0/, Start Date: 2024-01-12
Publisher:	Royal Society of Chemistry
ISSN:	2041-6520
Date of First Compliant Deposit:	18 January 2024
Date of Acceptance:	28 December 2023
Last Modified:	18 Mar 2024 13:01
URI:	https://orca.cardiff.ac.uk/id/eprint/165633

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