Generation of aziridinyllithiums from sulfinylaziridines with tert-butyllithium: Properties, reactivity, and application to a synthesis of alpha,alpha-Dialkylamino acid esters and amides including an optically active form

Aziridinyllithiums were generated from sulfinylaziridines by a sulfoxide-li thium exchange reaction of sulfoxides with tertbutyllithium at low temperat ure. The generated aziridinyllithiums were found to be stable in THF at bel ow -30 degrees C and they are reactive with several electrophiles such as c arbonyl compounds, ethyl chloroformate, and phenyl isocyanate. The reactivi ties of the aziridinyllithiums having several alkyl groups were investigate d. As an extension of this method, a synthesis of alpha,alpha-dialkylamino acid esters, including an optically active form, and amides was realized vi a the aziridinyllithiums. N-Non substituted alpha,alpha-dialkylamino acid e sters were synthesized starting from N-(4-methoxyphenyl) aldimine. (C) 2000 Elsevier Science Ltd. All rights reserved.