Enantioselective α-Nitroalkylation of Aldehydes Using SOMO Catalysis

Significance

The enantioselective α-nitroalkylation of aldehydes was achieved by reacting enolizable aldehydes with silyl nitronates in the presence of imidazolidinone catalyst 1 under oxidative conditions. The corresponding β-nitroaldehydes were obtained in good yields (up to 95%) and high enantioselectivities (er up to 98.5:1.5). The diastereoselectivity was controlled by simple variation of the reaction conditions and the nitronate. Two reasonable mechanistic scenarios for the formation of both diastereoisomers are proposed.