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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, Email: cushmanpharmacy.purdue.edu

H. Y. Kim, A. Talukdar, M. Cushman, Org. Lett., 2006, 8, 1085-1087.

DOI: 10.1021/ol0529703 (free Supporting Information)


Abstract

Biologically important N-β-hydroxyethylaziridine intermediates were conveniently prepared by regioselective ring-opening reactions of various epoxides with in situ-generated ethyleneimine  from β-chloroethylamine under basic conditions in an aqueous environment.

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Key Words

Aziridines, β-Amino Alcohols, Epoxides


ID: J54-Y2006-780