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Brønsted Acid-Promoted Olefin Aziridination and Formal anti-Aminohydroxylation

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journal contribution
posted on 09.02.2005 by Joseph M. Mahoney, Colin R. Smith, Jeffrey N. Johnston
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.

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