Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 23, Pages 17119-17128Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02241
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- KTH Royal institute of Technology
- Ministry of Education and Science of the Russian Federation [FZEN-2020-0022]
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Perfluorinated aromatic nitrenes can react with sulfinamides and sulfoxides to generate achiral and chiral SIAs and SOIs, with one enantiopure SIA serving as a novel chiral auxiliary in Grignard additions to imines, yielding the product in up to 96:4 diastereomeric ratio.
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.
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