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

Amie L. Williams and Jeffrey N. Johnston*

*Department of Chemistry & Vanderbilt Institute of Chemical Biology, Vanderbilt University, 2301 Vanderbilt Place, Nashville, TN 37235-1822, Email: jeffrey.n.johnstonvanderbilt.edu

A. L. Williams, J. N. Johnston, J. Am. Chem. Soc., 2004, 126, 1612-1613.

DOI: 10.1021/ja0385282 (free Supporting Information)


Abstract

A mild, convenient protocol for the synthesis of cis-aziridines employs a catalytic amount of Brønsted acid. Diazo compound decomposition via alkylation or homocoupling upon exposure to a proton source is slow relative to [2 + 1] annulation in the presence of a Schiff base.


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Key Words

Darzens Reaction, Aziridines


ID: J48-Y2004-1370