2023
DOI: 10.1002/ejoc.202300607
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Enantiomeric N‐(tert‐Butylsulfinyl) Polyfluoroalkyl Aldimines in aza‐Henry Reaction: Effective Route to Chiral Polyfluoroalkyl Nitroamines and Diamines

Abstract: A highly diastereoselective addition of nitromethane to the C=N bond of enantiomeric fluorine containing Ellman's aldimines, RFCH=NS(O)tert‐Bu (RF=CF3, CF2Br, C2F5, HC2F4), has been successfully developed. The synthetic potential of the resulting β‐nitrosulfinylamides was demonstrated through their conversion into optically active α‐fluoroalkylated 1,3‐nitroamines, 1,3‐diamines, and 4‐fluoroalkylated imidazolidin‐2‐ones.

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