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Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary
journal contribution
posted on 2021-11-12, 14:09 authored by Giampiero Proietti, Julius Kuzmin, Azamat Z. Temerdashev, Peter DinérSulfonimidamides
(SIAs) and sulfoximines (SOIs) have attracted
attention due to their potential in agriculture and in medicinal chemistry
as bioisosteres of biologically active compounds, and new synthetic
methods are needed to access and explore these compounds. Herein,
we present a light-promoted generation of perfluorinated aromatic
nitrenes, from perfluorinated azides, that subsequently are allowed
to react with sulfinamides and sulfoxides, generating achiral and
chiral SIAs and SOIs. One of the enantiopure SIAs was evaluated as
a novel chiral auxiliary in Grignard additions to the imines yielding
the product in up to 96:4 diastereomeric ratio.
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new synthetic methodsattracted attention dueaccessing perfluoroaryl sulfonimidamides4 diastereomeric rationovel chiral auxiliarychiral auxiliary sulfonimidamidesperfluorinated aromatic nitrenesbiologically active compoundsperfluorinated azideschiral siaspromoted generationmedicinal chemistryimines yieldinggrignard additionsgenerating achiral