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Xing, Xiangyou; O'Connor, Nicholas R; Stoltz, Brian M
Angewandte Chemie (International ed.), 09/2015, Volume: 54, Issue: 38Journal Article
The use of Oxone and a palladium(II) catalyst enables the efficient allylic CH oxidation of sterically hindered alpha-quaternary lactams which are unreactive under known conditions for similar transformations. This simple, safe, and effective system for CH activation allows for unusual tunable selectivity between a two-electron oxidation to the allylic acetates and a four-electron oxidation to the corresponding enals, with the dominant product depending on the presence or absence of water. The versatile synthetic utility of both the allylic acetate and enal products accessible through this methodology is also demonstrated.
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