Enantiomeric N‐(tert‐Butylsulfinyl) Polyfluoroalkyl Aldimines in aza‐Henry Reaction: Effective Route to Chiral Polyfluoroalkyl Nitroamines and Diamines

• DOI: 10.1002/ejoc.202300607
• Publication Date: 2023-07-17T08:24:54Z
• Authors: Yuliya V. Rassukana; Alona S. Cheredni...; Svitlana V. Shish...; Petro P. Onys'ko
• Keywords: Aldimine; Nitroaldol reaction

Abstract A highly diastereoselective addition of nitromethane to the C=N bond enantiomeric fluorine containing Ellman's aldimines, R F CH=NS(O) tert ‐Bu (R =CF 3 , CF 2 Br, C 5 HC 4 ), has been successfully developed. The synthetic potential 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.