The efficient production of single enantiomer nitrogen-containing compounds is important in fine chemical synthesis. In particular, methods that generate enantioenriched heterocycles are of interest to multiple chemical industries. Ring opening reactions of <i>meso</i>-aziridines generate chiral amine derivatives where the control of stereochemistry is possible through enantioselective catalysis. Palladium complexes for the enantioselective desymmetrization of <i>N</i>-acylaziridines are currently being developed in our laboratory. Stereocontrolled aziridine rearrangement to oxazolines and ring opening with nucleophiles will be discussed. These methods provide direct access to enantioenriched nitrogen-containing building blocks with up to 98% ee. Initial mechanistic investigations will discussed.

Palladium-catalyzed, enantioselective aziridine desymmetrization

251st National Meeting (2016)

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