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Chemoselective Alpha‐Deuteration of Amides via Retro‐ene Reaction
Author(s) -
Porte Vincent,
Di Mauro Giovanni,
Schupp Manuel,
Kaiser Daniel,
Maulide Nuno
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004103
Subject(s) - electrophile , amide , deuterium , chemistry , ene reaction , sulfoxide , functional group , alpha (finance) , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis , medicine , construct validity , physics , polymer , nursing , quantum mechanics , patient satisfaction
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.