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Chemoselective Alpha-Deuteration of Amides via Retro-ene Reaction.

ABSTRACT: A synthetically convenient approach for the direct ?-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.

SUBMITTER: Porte V 

PROVIDER: S-EPMC7756638 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Chemoselective Alpha-Deuteration of Amides via Retro-ene Reaction.

Porte Vincent V   Di Mauro Giovanni G   Schupp Manuel M   Kaiser Daniel D   Maulide Nuno N  

Chemistry (Weinheim an der Bergstrasse, Germany) 20201117 67

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. ...[more]

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