A new route to fluorine-containing aziridines and α-amino esters

The reaction of fluoroalkanesulfonyl azides with several silyl ketene acetals has been investigated. 1-Ethoxyl-1-trimethylsilyloxy-ethylene reacted readily with azides to afford N-fluoroalkanesulfonyl substituted glycinates in good yields. However, reaction of mono- or dialkyl-substituted silyl ketene acetals with azides gave rise to N-substituted α-amino esters and substituted N-perfluoroalkanesulfonyl aziridines. Acidic hydrolysis of the aziridines was also investigated. Mechanisms for the formation of the aziridines and α-amino esters are discussed.