Regioselective Synthesis of N-β-Hydroxyethylaziridines by the Ring-Opening Reaction of Epoxides with Aziridine Generated in Situ

Ha Young Kim, Arindam Talukdar, and Mark Cushman*
Department of Medicinal Chemistry and Molecular Pharmacology and the Purdue Cancer Center, School of Pharmacy and Pharmaceutical Sciences, Purdue University, West Lafayette, Indiana 47907
Org. Lett., 2006, 8 (6), pp 1085–1087
DOI: 10.1021/ol0529703
Publication Date (Web): February 24, 2006
Copyright © 2006 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.

, cushman@pharmacy.purdue.edu

Abstract

Abstract Image

Biologically important N-β-hydroxyethylaziridine intermediates were conveniently prepared by regioselective ring-opening reactions of diversely substituted epoxides. Ethyleneimine generated in situ under basic conditions from β-chloroethylamine was used as a nucleophile to open the epoxides in an aqueous environment.

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History

  • Published In Issue March 16, 2006
  • Received December 8, 2005

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