- Journal Article
Saturated nitrogen heterocycles can be found with increasing abundance in bioactive molecules despite a limited number of methods to access these scaffolds. However, the coupling of recently introduced SnAP [tin (Sn) amine protocol] reagents with a wide range of aldehydes and ketones has proven to be a reliable, practical, and versatile one-step approach to saturated N-heterocycles. While effective, the lack of mechanistic understanding limits efforts to develop new catalytic and enantioselective variants. To distinguish between a polar or radical mechanism, we assessed Lewis and Brønsted acids, radical trapping experiments, and radical clock SnAP reagents reinforcing the current understanding of the SnAP protocol as a radical cyclization. Show more
Journal / seriesSynlett
Pages / Article No.
SubjectSnAP reagents; N-heterocycles; morpholines; cyclization; radical clock; mechanism
Organisational unit03861 - Bode, Jeffrey W. / Bode, Jeffrey W.
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