Oxidative Deconstruction of Azetidinols to α‑Amino Ketones

A silver-mediated
synthesis of α-amino ketones via the oxidative
deconstruction of azetidinols has been developed using a readily scalable
protocol with isolated yields up to 80%. The azetidinols are easily
synthesized in one step and can act as protecting groups for these
pharmaceutically relevant synthons. Furthermore, mechanistic insights
are presented and these data have revealed that the transformation
is likely to proceed through the β-scission of an alkoxy radical,
followed by oxidation and C–N cleavage of the resulting α-amido
radical.