We have developed a diastereoselective copper-catalyzed alkynylation of cyclic β-(bromo)iminium ions, formed <i>in situ</i> from aminals, to deliver <i>trans</i>-difunctionalized products. The β-(bromo)aminal substrates are readily prepared via bromination of cyclic enamine precursors, allowing an efficient route from dihydropiperidines and pyrrolidines to highly functionalized heterocycles. Piperidine and pyrrolidine derivatives can be prepared with high diastereoselectivity and good functional group tolerance.

Diastereoselective alkynylations of β-(Bromo)iminium ions via copper(I) catalysis

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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