Naphthalene-Catalysed Reductive Opening of Aziridines with Lithium: A Direct Preparation of N-Lithio-2-lithioalkylamines

Article abstract of DOI:10.1016/0040-4039(93)85032-R

The reductive opening of N-phenylaziridine (1) with an excess of lithium powder in the presence of a catalytic amount (5 molar percent) of naphthalene at -78 deg C leads to the corresponding N-lithio-2-lithioethylamine (2), which by reaction with different electrophiles (water, deuterium oxide, dimethyl disulphide, pivalaldehyde or cyclohexanone) affords the expected products 3.The same process applied to N-cyclohexylaziridine fails.The reaction also works with the chiral aziridine 4 yielding the chiral deuteriated amine 5, through the corresponding chiral dianionic intermediate.