Brønsted Acid-Promoted Olefin Aziridination and Formal anti-Aminohydroxylation

Joseph M. Mahoney, Colin R. Smith, and Jeffrey N. Johnston*
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405
J. Am. Chem. Soc., 2005, 127 (5), pp 1354–1355
DOI: 10.1021/ja045608c
Publication Date (Web): January 11, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jnjohnst@indiana.edu

Abstract

Abstract Image

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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History

  • Published In Issue February 09, 2005
  • Received July 21, 2004

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