TBSOTf-promoted Umpolung C-C Coupling of Nitro Compounds

Ioffe et al. have reported the TBSOTf-promoted umpolung C-C coupling of nitro compounds. According to their results, the conversion of aliphatic nitro compounds into the corresponding silyl or alkyl nitronates followed by their C-C coupling with silyl ketene acetals under conditions of electrophilic catalysis with TBSOTf yields the corresponding nitroso acetals. The obtained nitroso acetals can be used as precursors of unnatural β"-amino acids.