Bronsted acid-promoted olefin aziridination and formal anti-aminohydroxylation.
A straightforward synthesis of aziridines is reported from an electron-rich azide (alkyl or aryl azide), electron-deficient olefin, and triflic acid in cold acetonitrile. The only coproduct of the reaction is dinitrogen (N2). Active ester substrates bearing a nucleophilic carbonyl engage the putative protonated aziridine intermediate to produce the product of olefin aminohydroxylation in which the nitrogen is benzyl protected and the oxygen is acylated. The possibility that a triazoline need not be an intermediate in aziridine production is advanced.
Mahoney
Joseph M
JM
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, IN 47405, USA.
Smith
Colin R
CR
Johnston
Jeffrey N
JN