51208-67-4Relevant academic research and scientific papers
Carbonyl 1,2-transposition through triflate-mediated a-amination
Wu, Zhao,Xu, Xiaolong,Wang, Jianchun,Dong, Guangbin
, p. 734 - 740 (2021/11/16)
To date, it remains challenging to selectively migrate a carbonyl oxygen within a given molecular scaffold, especially to an adjacent carbon. In this work, we describe a simple one- or two-pot protocol that transposes a ketone to the vicinal carbon. This approach first converts the ketone to the corresponding alkenyl triflate, which can then undergo the palladium- and norbornene-catalyzed regioselective a-amination and ipso-hydrogenation enabled by a bifunctional hydrogen and nitrogen donor. The resulting "transposed enamine" intermediate can subsequently be hydrolyzed to produce the 1,2-carbonyl-migrated product. This method allows rapid access to unusual bioactive analogs through late-stage functionalization.
