Selenoxide Elimination Triggers Enamine Hydrolysis to Primary and Secondary Amines: A Combined Experimental and Theoretical Investigation.
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ABSTRACT:
SUBMITTER: Ribaudo G
PROVIDER: S-EPMC8125833 | biostudies-literature | 2021 May
REPOSITORIES: biostudies-literature
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Selenoxide Elimination Triggers Enamine Hydrolysis to Primary and Secondary Amines: A Combined Experimental and Theoretical Investigation.
Ribaudo Giovanni G Bortoli Marco M Oselladore Erika E Ongaro Alberto A Gianoncelli Alessandra A Zagotto Giuseppe G Orian Laura L
Molecules (Basel, Switzerland) 20210508 9
We discuss a novel selenium-based reaction mechanism consisting in a selenoxide elimination-triggered enamine hydrolysis. This one-pot model reaction was studied for a set of substrates. Under oxidative conditions, we observed and characterized the formation of primary and secondary amines as elimination products of such compounds, paving the way for a novel strategy to selectively release bioactive molecules. The underlying mechanism was investigated using NMR, mass spectrometry and density fun ...[more]
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