Generation of Aziridinyllithiums from Sulfinylaziridines with tert-Butyllithium: Properties, Reactivity, and Application to a Synthesis of α,α-Dialkylamino Acid Esters and Amides Including an Optically Active Form

Aziridinyllithiums were generated from sulfinylaziridines by a sulfoxide–lithium exchange reaction of sulfoxides with tert-butyllithium at low temperature. The generated aziridinyllithiums were found to be stable in THF at below −30°C and they are reactive with several electrophiles such as carbonyl compounds, ethyl chloroformate, and phenyl isocyanate. The reactivities of the aziridinyllithiums having several alkyl groups were investigated. As an extension of this method, a synthesis of α,α-dialkylamino acid esters, including an optically active form, and amides was realized via the aziridinyllithiums. N-Non substituted α,α-dialkylamino acid esters were synthesized starting from N-(4-methoxyphenyl) aldimine.