The Brønsted Acid-Catalyzed Direct Aza-Darzens Synthesis of N-Alkyl cis-Aziridines

Amie L. Williams and Jeffrey N. Johnston*
Department of Chemistry, Indiana University, Bloomington, Indiana 47405-7102
J. Am. Chem. Soc., 2004, 126 (6), pp 1612–1613
DOI: 10.1021/ja0385282
Publication Date (Web): January 27, 2004
Copyright © 2004 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

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A mild protocol for the synthesis of cis-aziridines is described that employs a catalytic amount of Brønsted acid. Despite the potential for diazo compound decomposition via alkylation or homocoupling upon exposure to a proton source, these pathways are slow relative to [2 + 1] annulation in the presence of a Schiff base, leading to aziridine product. The process uses no metals or reagents that must be removed chromatographically, exhibits rapid turnover rates, and produces only atomic nitrogen as a coproduct. High levels of relative stereocontrol are also possible when forming the Schiff base from a chiral nonracemic aldehyde.

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History

  • Published In Issue February 18, 2004
  • Received September 15, 2003

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