Our novel phenanthroline ligands with Fe(OTf)2 enables the catalytic asymmetric epoxidation of acyclic �,�-disubstituted enones which have been heretofore inaccessible substrate classes. The reactions provide highly enantioenriched a,�-epoxyketones (up to 92% ee) which are further converted to functionalized �-ketoaldehydes and 2-isooxazolidines with quaternary centers. It is noteworthy that our system gives diastereomerically pure epoxide while the conventional method to synthesize epoxides from �,�-disubstituted enones, such as Weitz-Scheffer type epoxidation, suffers from low diastereocontrol.

Iron-catalyzed asymmetric epoxidation of β,β-disubstituted enones

243rd National Meeting (2012)

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