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Literature DB >> 33035360

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

Vincent Porte¹, Giovanni Di Mauro¹, Manuel Schupp^1,2, Daniel Kaiser¹, Nuno Maulide^1,2.

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.

Entities: Chemical

Keywords: amide activation; chemoselectivity; deuteration; sulfoxide isotopic labelling

Year: 2020 PMID： 33035360 PMCID： PMC7756638 DOI： 10.1002/chem.202004103

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.020

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

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