Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary

Autor:	Peter Dinér, Julius Kuzmin, Giampiero Proietti, A. Z. Temerdashev
Rok vydání:	2021
Předmět:	Chiral auxiliary chemistry.chemical_compound Enantiopure drug Chemistry Chemistry Pharmaceutical Nitrene Organic Chemistry Diastereomer Imines Combinatorial chemistry Article
Zdroj:	The Journal of Organic Chemistry
ISSN:	1520-6904 0022-3263
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::968aebf8828da074f0ebe9ab2a2850be https://doi.org/10.1021/acs.joc.1c02241 Zobrazit plný text záznamu