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Chemoselective Alpha-Deuteration of Amides via Retro-ene Reaction |
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| Authors: | Vincent Porte Giovanni Di Mauro Manuel Schupp Dr. Daniel Kaiser Prof. Dr. Nuno Maulide |
| Affiliation: | 1. Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria;2. Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria These authors contributed equally to this work.;3. Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria CeMM—Research Center for Molecular Medicine, Austrian Academy of Sciences, Lazarettgasse 14, AKH BT 25.3, 1090 Vienna, Austria These authors contributed equally to this work. |
| Abstract: | A synthetically convenient approach for the direct α-deuteration of amides is reported. This mechanistically unusual process relies on a retro-ene-type process, triggered by the addition of deuterated dimethyl sulfoxide to a keteniminium intermediate, generated through electrophilic amide activation. The transformation displays broad functional-group tolerance and high deuterium incorporation. |
| Keywords: | amide activation chemoselectivity deuteration sulfoxide isotopic labelling |