This synthesis reveals a novel method for constructing 2,6-diazabicyclo[3.3.1]nonanes using nitrones, suggesting potential applications in diamine scaffolds.
A new synthesis route to 2,6-diazabicyclo[3.3.1]nonanes as a scaffold of conformationally restricted diamines is disclosed. Starting from 4-amino-1-Boc-piperidine (Boc = tert-butoxycarbonyl), introduction of an alkene unit on the 4-amino group, followed by removal of the Boc group, afforded secondary amines. Subsequent oxidation of the amines with Oxone furnished nitrones, which underwent intramolecular cycloaddition to construct the 2,6-diazabicyclo[3.3.1]nonane skeleton.
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Kawai et al. (2025) studied this question.
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