Asymmetric Aza-Henry Reactions from N-p-Tolylsulfinylimines

N-Sulfinylimines derived from aromatic or aliphatic aldehydes and ketones react with nitromethane and NaOH in a highly diastereoselective manner under mild conditions. In the presence of TBAF, the reaction rates are strongly increased and the stereoselectivity is inverted. This method provides enantiomerically pure β-nitroamines derived from enolizable aldimines and ketimines, which so far are hardly accessible by aza-Henry reactions.