Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary
journal contributionposted on 2021-11-12, 14:09 authored by Giampiero Proietti, Julius Kuzmin, Azamat Z. Temerdashev, Peter Dinér
Sulfonimidamides (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.
new synthetic methodsattracted attention dueaccessing perfluoroaryl sulfonimidamides4 diastereomeric rationovel chiral auxiliarychiral auxiliary sulfonimidamidesperfluorinated aromatic nitrenesbiologically active compoundsperfluorinated azideschiral siaspromoted generationmedicinal chemistryimines yieldinggrignard additionsgenerating achiral