Regio- and Stereoselective Monoamination of Diketones without Protecting Groups

摘要

Regioselective transformations are highly desirable in organic synthesis, since they allow for the differentiation between two or more (chemically identical) reactive centers, which is otherwise only possible by employing sophisticated and laborious protection strategies. However, protecting-group-free strategies are superior and have received outstanding merits for their successes. Although the regioselective animation of, for example, alkanes, allylic systems,or indoles, has been recently described, the regioselective asymmetric bioamination of diketones has not yet been reported, to the best of our knowledge. For example, diketones, such as 1,5-diketo compounds, may serve as possible precursors for a chiral piperidine scaffold. Consequently, we chose 2,6-diketones 1 as model substrates to investigate the possible asymmetric regioselective amination employing ω-transaminases (ω-TAs; Scheme 1).inases